CAFFEIC ACID
Caffeic acid is a naturally occurring phenolic compound found in plants like coffee, fruits, and vegetables, known for its potent antioxidant and anti-inflammatory properties.
In pharmaceuticals, caffeic acid is valued for its potential to combat oxidative stress, reduce inflammation, and provide antimicrobial effects.
Caffeic acid also plays a role in agriculture as a growth regulator and natural pesticide, demonstrating its versatility across various industries.
CAS Number: 331-39-5
EC Number: 206-361-2
Chemical Formula: C9H8O4
Molar Mass: 180.16 g/mol
Synonyms: RARECHEM BK HC T335, TIMTEC-BB SBB006475, 4-(2’-carboxyvinyl)-1,2-dihydroxybenzene, 4-(2-Carboxyethenyl)-1,2-dihydroxybenzene, 4-(2'-Carboxyvinyl)-1,2-dihydroxybenzene, CAFFEIC ACID, 3-(3,4-DIHYDROXYPHENYL)-2-PROPENOIC ACID, 3-(3,4-DIHYDROXYPHENYL)ACRYLIC ACID, Caffeicacid,96%, CAFFEIC ACID, MATRIX SUBSTANCE FOR MALDI -MS, 3,4-DIHYDROXYCINNAMIC ACID, 97%, PREDOMINANTLY TRANS, 3,4-DIHYDROXYCINNAMIC ACID (CAFFEIC ACID), CaffeicAcidPure, CAFFIC ACID, 3,4-Dihydroxycinnamic acid, predominantly trans isomer, 99+%, LABOTEST-BB LT00233168, 3,4-DIHYDROXYCINNAMIC ACID, AKOS B004050, NSC 623438, (Z)-3-(3,4-dihydroxyphenyl)acrylic acid, Caffeic, CAFFEICACID(BULK, Caffeic acid 0, (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoic acid, Caffeic acid, 99%, predoMinantly trans, Caffeic acid, predoMinantly trans, (2E)-3-(3,4-Dihydroxyphenyl)-2-propenoic acid, 2-Propenoic acid, 3-(3,4-dihydroxyphenyl)-, 3-(3,4-dihydroxyphenyl)-2-propenoicaci, 3-(3,4-Dihydroxyphenyl)propenoic acid, 3,4-Dihydroxybenzeneacrylic acid, 3,4-dihydroxybenzeneacrylicacid, 3,4-dihydroxy-cinnamicaci, 3,4-dihydroxycinnamicacid,predominantlytransisomer, CAFFEIC ACID(AHP), 3,4-Dihydroxycinnamic acid, 99+%, predominantly trans isomer, CINNAMICACID,3,4-DIHYDROXY-, CAFFEIC ACID NATURAL, CAFFEIC ACID SYNTHETIC, (E)-3-(3,4-Dihydroxyphenyl)acrylic acid, (E)-3,4-Dihydroxycinnamic acid, 3,4-Dihydroxy-trans-cinnamic acid, trans-Caffeic acid, 3,4-Dihydroxycinnamic acid, 99%, predominantly trans, 3,4-Dihydroxycynnamic acid, 3,4-Dihydroxycinnamic acid, predominantly trans, 99%, 3,4-dihydroxyben, Caffeic acid ,99%, 3,4-dihydroxy-acid, Caffeic acid, 3-(3,4-Dihydroxyphenyl)prop-2-enoic acid, 3-(3,4-Dihydroxyphenyl)acrylic acid, 3,4-DihydroxycinnaMic acid, predoMinantly trans isoMer, 99+% 25GR, 3,4-DihydroxycinnaMic acid, predoMinantly trans isoMer, 99+% 5GR, Caffeic Acid 〔3,4-Dihydroxycinnamic Acid〕, Caffeic acid purum, >=95.0% (HPLC), 3,4-Dihydroxycinnamic acid for synthesis, Caffeic Acid - CAS 331-39-5 - Calbiochem, Caffeic acid 331-39-5, (E)-3-(3,4-dihydroxyphenyl)-2-propenoate, caffeic acid, 3,4-Dihydroxycinnamic acid, 331-39-5, 501-16-6, 3-(3,4-dihydroxyphenyl)acrylic acid, trans-caffeic acid, 3,4-Dihydroxybenzeneacrylic acid, (E)-3-(3,4-dihydroxyphenyl)acrylic acid, (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoic acid, (E)-3,4-dihydroxycinnamic acid, 3,4-Dihydroxy-trans-cinnamate, 2-Propenoic acid, 3-(3,4-dihydroxyphenyl)-, 3-(3,4-Dihydroxyphenyl)propenoic acid, Cinnamic acid, 3,4-dihydroxy-, UNII-U2S3A33KVM, 3-(3,4-Dihydroxyphenyl)-2-propenoic acid, 4-(2'-Carboxyvinyl)-1,2-dihydroxybenzene, 4-(2-Carboxyethenyl)-1,2-dihydroxybenzene, NSC 57197, 3-(3,4-Dihydroxy phenyl)-2-propenoic acid, 2-Propenoic acid, 3-(3,4-dihydroxyphenyl)-, (E)-, 3,4-Dihydroxycinnamic acid, predominantly trans, (2E)-3-(3,4-dihydroxyphenyl)acrylic acid, (E)-3-(3,4-dihydroxyphenyl)prop-2-enoic acid, Caffeicacid, 71693-97-5, 3-(3,4-dihydroxyphenyl)prop-2-enoic acid, Caffeic acid - Natural, CCRIS 847, HSDB 7088, SR-01000000203, EINECS 206-361-2, Caffeic acid dehydrogenation homopolymer, CHEBI:36281, 3,4-Dihydroxycinnamic acid, 99+%, predominantly trans isomer, caffeic-acid, Caffeic acid, 1, Caffeic acid polymer, Caffeic Acid,(S), PubChem8262, Caffeic acid, trans-, CAFFEIC ACID natural, 2-Propenoic acid,3-(3,4-dihydroxyphenyl)-, (2E)-, 3,4-Dihydroxycinnamate, XVII, 3-(3,4-Dihydroxyphenyl)-2-propenoic acid, homopolymer, ZINC58172, 2-Propenoic acid, 3-(3,4-dihydroxyphenyl)-, homopolymer, Caffeic Acid - CAS 331-39-5, Caffeic acid, >=98.0% (HPLC), 2-Propenoic acid,4-dihydroxyphenyl)-, Caffeic acid, purum, >=95.0% (HPLC), 2-Morpholin-4-yl-isonicotinicacidhydrochloride, (2E)-3-(3,4-Dihydroxyphenyl)-2-propenoic acid, 3-(3,4-Dihydroxyphenyl)-2-propenoic acid polymer, 2-Propenoic acid, 3-(3,4-dihydroxyphenyl)- (9CI), 2-Propenoic acid, 3-(3,4-dihydroxyphenyl)-, (2E)-, F3096-1708, 8B3E4DA7-F3B0-4972-A315-2E387071737F, trans-Caffeic acid, certified reference material, TraceCERT(R), Caffeic acid, matrix substance for MALDI-MS, >=99.0% (HPLC), Caffeic acid, United States Pharmacopeia (USP) Reference Standard, Caffeic acid, matrix substance for MALDI-MS, >=99.0% (HPLC), powder, light beige, 331-89-5
Caffeic acid is a naturally occurring phenolic compound widely found in plants, including coffee, fruits, and vegetables.
Caffeic acid is known for its potent antioxidant and anti-inflammatory properties, which make it valuable in various health-related applications.
In pharmaceuticals, caffeic acid is used for its potential to combat oxidative stress, reduce inflammation, and provide antimicrobial effects.
Caffeic acid also finds extensive use in the food and beverage industry, where it enhances flavor, acts as a natural preservative, and is included in dietary supplements for its health benefits.
In cosmetics, caffeic acid contributes to anti-aging formulations by protecting the skin from damage and improving skin tone.
Additionally, its role extends to agriculture, where Caffeic acid functions as a growth regulator and natural pesticide.
Caffeic acid’s diverse applications underscore its importance as a versatile and beneficial compound in numerous industries.
Caffeic acid is an organic compound that is classified as a hydroxycinnamic acid.
This yellow solid consists of both phenolic and acrylic functional groups.
Caffeic acid is found in all plants because it is an intermediate in the biosynthesis of lignin, one of the principal components of woody plant biomass and its residues.
Caffeic acid is a kind of polyhydroxy styrene acid, with the general chemical properties of phenolic acid.
Caffeic acid is easily oxidized for the reason of the unsaturated double bonds, particularly unstable in alkaline solution
Caffeic acid has both cis and trans isomers, and the two isomers of caffeic acid have a mutual transformation in plants, which may regulate some important physiological process.
Caffeic acid exists in plants in the main form of complexes; free state accounts for a few proportion.
Caffeic acid exists in its free and ester form.
Caffeic acid is considered as the predominant polyphenol, contributing to the hydroxycinnamic acid content in various fruits.
Coffee is one of the major source of caffeic acid.
Caffeic acid is an organic compound with the formula (HO)2C6H3CH=CHCO2H.
Caffeic acid is a polyphenol.
Caffeic acid is a yellow solid.
Structurally, Caffeic acid is classified as a hydroxycinnamic acid.
The molecule consists of both phenolic and acrylic functional groups.
Caffeic acid is found in all plants as an intermediate in the biosynthesis of lignin, one of the principal components of biomass and its residues.
Caffeic acid is unrelated to caffeine.
Caffeic acid is a type of phenolic acid found in many plants and foods, such as apples and red wine.
Coffee is the main source of caffeic acid in the diet.
Caffeic acid might have antioxidant and anti-inflammatory effects.
Caffeic acid might also have effects on the immune system.
People use caffeic acid for athletic performance, obesity, and other purposes, but there is no good scientific evidence to support these uses.
Caffeic Acid is an endogenous phenolic phytochemical compound that exists in plants and many foods.
A major metabolite product upon hydrolization of chlorogenic acid caffeic acid inhibits a number of lipoxygenases such as 5-LO (5-lipoxygenase), in a non-competitive manner, and 12-LO (12-lipoxygenase) inhibiting leukotriene synthesis resulting in further inhibition of immunoregulation.
Caffeic Acid has also been shown to inhibit arachidonic acid metabolism in platelets at high doses.
Caffeic acid has been observed to stimulate prostaglandin synthesis at high doses.
Caffeic Acid is an inhibitor of GST, ODC, Tyk and Xanthine Oxidase.
Caffeic acid is an organic compound and a potent antioxidant.
Caffeic acid can be found naturally in a wide range of plants.
Caffeic acid is a type of polyphenol, a class of micronutrients known for their antioxidant properties.
The nutrient is claimed to have many health benefits, including anti-inflammatory, anticancer, and antiviral abilities.
Caffeic acid may help boost the performance of athletes.
However, it isn’t considered “essential” for human health.
In other words, you don’t need Caffeic acid to survive.
The most common source of caffeic acid in the human diet is from drinking coffee.
Caffeic acids also found in certain vegetables, fruits, and herbs.
Some examples of foods containing caffeic acid include:
Coffee
Wine
Turmeric
Basil
Thyme
Oregano
Sage
Cabbage
Apples
Strawberries
Cauliflower
Radishes
Mushrooms
Kale
Pears
Olive oil
Despite its name, caffeic acid is unrelated to caffeine.
Applications of Caffeic Acid:
Caffeic acid has been used as a standard of phenolic acid in the study to determine the total phenolic acid content in vegetables after subjecting to alkaline and acid hydrolysis.
Caffeic acid has also been used to determine its antioxidant activity by various assay methods.
Caffeic acid is a versatile compound with numerous applications across various fields.
In pharmaceuticals, Caffeic acid is utilized for its antioxidant and anti-inflammatory properties, aiding in the management of chronic diseases and neurodegenerative conditions.
In the food and beverage industry, Caffeic acid enhances flavor and acts as a natural preservative.
Caffeic acid's role in cosmetics includes reducing signs of aging and soothing irritated skin.
Additionally, caffeic acid serves as a plant growth regulator and potential pesticide in agriculture, while also being explored in research for its biochemical benefits and environmental applications in bioremediation.
Caffeic acid is safe to be applied in cosmetics and has a broader antibacterial and antiviral activity.
Caffeic acid can also absorb ultraviolet radiation.
A low concentration of Caffeic acid already has inhibitory efficacy on the generation of skin melanin.
Caffeic acid's applied amount in the beauty products for whitening is at the range of 0.5 to 2%.
Caffeic acid can also be used as additive for the oxidized hair dyes which is good for enhancing the strength of the color.
Uses of Caffeic Acid:
Caffeic acid is a multifaceted phenolic compound with a wide range of applications owing to its powerful antioxidant, anti-inflammatory, and antimicrobial properties.
In the pharmaceutical and healthcare sectors, Caffeic acid plays a crucial role in protecting cells from oxidative stress, reducing inflammation, and offering antimicrobial benefits, which can aid in managing chronic diseases, neurodegenerative conditions, and various infections.
In the food and beverage industry, caffeic acid is valued for enhancing flavor, preserving food quality, and providing health benefits through dietary supplements.
Caffeic acid's use in cosmetics and personal care products leverages its anti-aging and skin-soothing properties, making Caffeic acid a popular ingredient in skincare formulations.
Additionally, in agriculture, caffeic acid acts as a natural growth regulator and potential pesticide, while in research and development, Caffeic acid contributes to understanding disease mechanisms and developing new treatments.
Caffeic acid's environmental applications also extend to bioremediation, highlighting its versatility and significance across multiple fields.
Caffeic acid is a versatile phenolic compound found in many plants and used in various applications due to its antioxidant, anti-inflammatory, and antimicrobial properties.
Here are some of the key uses of caffeic acid:
Pharmaceuticals and Healthcare:
Antioxidant Activity:
Caffeic acid is known for its powerful antioxidant properties, which help in neutralizing free radicals and protecting cells from oxidative damage.
This makes Caffeic acid valuable in preventing and managing chronic diseases like cancer and cardiovascular diseases.
Anti-inflammatory Effects:
Caffeic acid can reduce inflammation and is used in treating conditions like arthritis and other inflammatory diseases.
Antimicrobial Properties:
Caffeic acid exhibits antimicrobial activity against a variety of pathogens, including bacteria and fungi, making Caffeic acid useful in developing new antimicrobial agents.
Neuroprotective Effects:
Research suggests that caffeic acid may help protect the brain from neurodegenerative diseases such as Alzheimer’s and Parkinson’s by reducing oxidative stress and inflammation.
Skin Care:
Caffeic acid is incorporated into skin care products for its antioxidant and anti-inflammatory properties, which help in protecting the skin from damage and reducing signs of aging.
Food and Beverage Industry:
Flavor Enhancer:
Caffeic acid contributes to the flavor profile of various foods and beverages, including coffee and certain fruits, by providing a characteristic bitter taste.
Preservative:
Caffeic acid's antioxidant properties help in preserving the quality and extending the shelf life of food products by preventing oxidation and rancidity.
Nutritional Supplements:
Caffeic acid is included in dietary supplements due to its potential health benefits, including improving overall health and supporting immune function.
Cosmetics and Personal Care:
Anti-Aging:
In cosmetics, caffeic acid is used for its ability to scavenge free radicals and reduce signs of aging, such as wrinkles and fine lines.
Skin Brightening:
Caffeic acid helps in reducing skin pigmentation and promoting a more even skin tone.
Anti-Inflammatory:
Caffeic acid can soothe and calm irritated skin, making it suitable for sensitive skin care products.
Agriculture:
Plant Growth Regulator:
Caffeic acid plays a role in plant growth and development and can be used as a natural growth regulator.
Pesticide:
Due to its antimicrobial properties, Caffeic acid has potential use as a natural pesticide or fungicide in agriculture.
Research and Development:
Pharmacological Studies:
Caffeic acid is a subject of various pharmacological studies to understand its effects on health and disease mechanisms, leading to potential new therapeutic uses.
Biochemical Research:
Caffeic acid is used in research to study the mechanisms of oxidative stress and inflammation, contributing to the development of new drugs and treatments.
Environmental Applications:
Bioremediation:
Caffeic acid may be used in environmental applications for bioremediation, where it helps in the degradation of pollutants and contaminants in the soil and water.
Other uses:
Caffeic acid may be the active ingredient in caffenol, a do-it-yourself black-and-white photographic developer made from instant coffee.
The developing chemistry is similar to that of catechol or pyrogallol.
Caffeic acid is also used as a matrix in MALDI mass spectrometry analyses.
Benefits of Caffeic Acid:
Caffeic acid is a known antioxidant.
Antioxidants help prevent the oxidation of other molecules in the body.
Oxidation produces free radicals, which can damage cells.
This in turn can lead to inflammation, heart disease, or even cancer.
Caffeic acid is also claimed to:
reduce inflammation
prevent cancer
prevent toxicity associated with chemotherapy and radiation
prevent diabetes
prevent premature aging
prevent neurodegenerative diseases, like Parkinson’s disease
reduce exercise-related fatigue
Like other antioxidants, caffeic acid may be helpful in improving overall health as we age.
Caffeic acid's antioxidant properties may help reduce chances of developing cancer, heart disease, and other illnesses of old age, like Alzheimer’s disease.
In addition, Caffeic acid may keep skin looking younger by protecting it from damage from the sun.
Boosting athletic performance:
A small studyTrusted Source was performed to see if caffeic acid could help competitive athletes during prolonged periods of endurance exercise.
The study used caffeic acid phenethyl ester (CAPE), a caffeic acid derivative.
After extracting cells from the blood of competitive cyclists, some of the cells were treated with CAPE, while others were not.
Then all of the cells were subjected to hyperthermal (heat) stress.
The researchers found that cells treated with CAPE were better able to handle and recover from the stress.
More research is needed to replicate these findings outside of the laboratory.
Another study found that caffeic acid improved exercise tolerance and reduced markers of fatigue associated with exercise in rats.
Preventing diabetes:
One study found that caffeic acid was able to significantly reduce blood sugar levels in mice with diabetes compared to a control group.
More research in humans is needed.
Reducing cancer risk:
ResearchTrusted Source on coffee has shown a link between regular consumption of coffee and incidence of certain types of cancer compared to people who don’t drink coffee.
Studies have suggested that daily coffee intake, including decaffeinated coffee, is associated with a reduced incidence of colon and rectal cancer.
Researchers think that these effects are attributed to polyphenol compounds, like caffeic acid.
Anti-aging:
Due to its antioxidant and anti-inflammatory properties, caffeic acid is often found in skin care regimens.
Studies show promising results.
A studyTrusted Source in mice, for example, found that caffeic acid from garlic applied topically to the skin of mice successfully prevented wrinkle formation induced by UVB irradiation.
Caffeic acid also inhibited oxidative stress.
The authors concluded that caffeic acid shows potential as an active ingredient for skin treatments against UVB-induced skin damage.
Enhancing cancer treatment:
Many drugs used to treat cancer, such as chemotherapy and radiation, can result in unintended damage to organs, including the kidneys and liver.
Several studies performed in rats or using extracted human cells have shown promise in using caffeic acid derivatives to help reduce the toxicity associated with certain cancer treatments.
This may lead to better outcomes.
Treating HIV:
Caffeic acid and its derivatives have been shown to inhibit the virus known as HIV.
While researchers don’t propose using caffeic acid alone to treat HIV, they suggest that including more caffeic acid-rich foods in the diet could help improve overall treatment for the infection.
More research is needed to confirm these benefits.
Other benefits:
Further areas where caffeic acid might be beneficial include:
Chronic inflammation:
Caffeic acid’s anti-inflammatory power is one way it might fight or prevent cancer.
A 1996 study found that caffeic acid could target a specific source of inflammation, both in a petri dish and in the human body.
Another, more recent study in 2013 showed that caffeic acid strongly suppresses inflammatory enzymes.
Diabetes:
Research in mice has found that caffeic acid may combat some effects of diabetes.
A 2009 studyTrusted Source of diabetic mice found that caffeic acid could raise blood insulin levels, lower blood glucose, and fight inflammation.
Caffeic acid also reduced the risk of a dangerous blood clot and lowered triglycerides, which are associated with clogged arteries and heart disease.
Occurrences of Caffeic Acid:
Natural occurrences:
Caffeic acid can be found in the bark of Eucalyptus globulus the barley grain Hordeum vulgare and the herb Dipsacus asperoides.
Caffeic acid can also be found in the freshwater fern Salvinia molesta and in the mushroom Phellinus linteus.
Occurrences in food:
Free caffeic acid can be found in a variety of beverages, including brewed coffee at 63.1-96.0 mg per 100 ml and red wine at 2 mg per 100 ml.
Caffeic acid is found at relatively high levels in herbs of the mint family, especially thyme, sage and spearmint (at about 20 mg per 100 g), and in spices, such as Ceylon cinnamon and star anise (at about 22 mg per 100 g).
Caffeic acid occurs at moderate levels in sunflower seeds (8 mg per 100 g), apple sauce, apricots and prunes (at about 1 mg per 100 g).
Caffeic acid occurs at remarkably high levels in black chokeberry (141 mg per 100 g).
Caffeic acid is also quite high in the South American herb yerba mate (150 mg per 100 g based on thin-layer chromatography densitometry and HPLC).
Caffeic acid is also found at lower levels in barley and rye.
Biosynthesis:
Caffeic acid is biosynthesized by hydroxylation of coumaroyl ester of quinic acid (esterified through a side chain alcohol).
This hydroxylation produces the caffeic acid ester of shikimic acid, which converts to chlorogenic acid.
Caffeic acid is the precursor to ferulic acid, coniferyl alcohol, and sinapyl alcohol, all of which are significant building blocks in lignin.
The transformation to ferulic acid is catalyzed by the enzyme caffeate O-methyltransferase.
Caffeic acid and its derivative caffeic acid phenethyl ester (CAPE) are produced in many kinds of plants.
Dihydroxyphenylalanine ammonia-lyase was presumed to use 3,4-dihydroxy-L-phenylalanine (L-DOPA) to produce trans-caffeate and NH3.
However, the EC number for this purported enzyme was deleted in 2007, as no evidence has emerged for its existence.
Biotransformation:
Caffeate O-methyltransferase is an enzyme responsible for the transformation of caffeic acid into ferulic acid.
Caffeic acid and related o-diphenols are rapidly oxidized by o-diphenol oxidases in tissue extracts.
Biodegradation:
Caffeate 3,4-dioxygenase is an enzyme that uses caffeic acid and oxygen to produce 3-(2-carboxyethenyl)-cis,cis-muconate.
Caffeic acid is susceptible to autoxidation.
Glutathione and thiol compounds (cysteine, thioglycolic acid or thiocresol) or ascorbic acid have a protective effect on browning and disappearance of caffeic acid.
This browning is due to the conversion of o-diphenols into reactive o-quinones.
Chemical oxidation of caffeic acid in acidic conditions using sodium periodate leads to the formation of dimers with a furan structure (isomers of 2,5-(3′,4′-dihydroxyphenyl)tetrahydrofuran 3,4-dicarboxylic acid).
Caffeic acid can also be polymerized using the horseradish peroxidase/H2O2 oxidizing system.
Glycosides of Caffeic Acid:
3-O-caffeoylshikimic acid (dactylifric acid) and Caffeic acid's isomers, are enzymic browning substrates found in dates (Phoenix dactylifera fruits).
Pharmacology of Caffeic Acid:
Caffeic acid has a variety of potential pharmacological effects in in vitro studies and in animal models, and the inhibitory effect of caffeic acid on cancer cell proliferation by an oxidative mechanism in the human HT-1080 fibrosarcoma cell line has recently been established.
Caffeic acid is an antioxidant in vitro and also in vivo.
Caffeic acid also shows immunomodulatory and anti-inflammatory activity.
Caffeic acid outperformed the other antioxidants, reducing aflatoxin production by more than 95 percent.
The studies are the first to show that oxidative stress that would otherwise trigger or enhance Aspergillus flavus aflatoxin production can be stymied by caffeic acid.
This opens the door to use as a natural fungicide by supplementing trees with antioxidants.
Biochem/physiol Actions of Caffeic Acid:
A natural dietary phenolic compound found in plants that is an anti-oxidant.
Inhibits the synthesis of leukotrienes that are involved in immunoregulation, inflammation and allergy.
Inhibits Cu2+-induced LDL oxidation.
Caffeic acid and other polyphenols are metabolized by going through enzyme catalysed methyl transfer, sulfation and glucuronic acid addition.
Caffeic acid non-competitively prevents the action of 5-lipoxygenase.
Caffeic acid ready undergoes hydrolysis in alkaline conditions.
Chemistry of Caffeic Acid:
Caffeic acid is susceptible to autoxidation.
With transition metals, Caffeic acid forms transition metal-carboxylate complexes, but not salts.
Glutathione and thiol compounds (cysteine, thioglycolic acid or thiocresol) or ascorbic acid have a protective effect on browning and disappearance of caffeic acid.
This browning is due to the conversion of o-diphenols into reactive o-quinones.
Chemical oxidation of caffeic acid in acidic conditions using sodium periodate leads to the formation of dimers with a furan structure (isomers of 2,5-(3′,4′-dihydroxyphenyl)tetrahydrofuran 3,4-dicarboxylic acid).
Caffeic acid can also be polymerized using the horseradish peroxidase/H2O2 oxidizing system.
Isomers:
Isomers with the same molecular formula and in the hydroxycinammic acids family are:
Umbellic acid (2,4-dihydroxycinnamic acid)
2,3-Dihydroxycinnamic acid
2,5-Dihydroxycinnamic acid
Physical and Chemical Properties of Caffeic Acid:
Caffeic acid, scientific name: "3-(3,4-dihydroxyphenyl)-2-propenoic acid."
Caffeic acid is presented in plants such as coffee in the form of chlorogenic acid.
Caffeic acid is yellow crystals with melting point being 223~225 °C.
When Caffeic acid is precipitated in concentrated solution, it contains no crystal water.
However, precipitate of crystals from dilute solution contains one molecule of crystallized water.
Caffeic acid is slightly soluble in water, and easily soluble in hot water, cold ethanol, and ethyl acetate.
Caffeic acid's alkaline solution is orange and exhibits dark green when being mixed with ferric chloride.
Extraction Method of Caffeic Acid:
Caffeic acid belongs to common phenolic compounds with effects of increasing the levels of white blood cells.
Caffeic acid is easily to be confused with caffeine and is widely distributed in the plant kingdom.
Caffeic acid's major plant sources include lemon peel, Ranunculaceae cimicifuga rhizome, and valerian root.
Caffeic acid, together with ferulic acid, erucic acid, and p-hydroxy cinnamic acid are ubiquitous hydroxy cinnamic acid-class molecule distributed in various kinds of plants.
This kind of products has conjugated double bonds in the side chain of the molecular structure, and thus exhibiting significant fluorescence upon ultraviolet light, mostly showing bluish color fluorescence.
This is a advantage for paper chromatography tests or thin layer chromatography tests.
Single spike cimicifuga rhizome is extracted with methanol which is removed through concentration under reduced pressure.
Add hot water to the residue to dissolve Caffeic acid.
Heating the water to dissolve the residue, and further filter the insolubles upon heating.
After cooling, add benzene for extraction with the benzene solution being washed with 1% aqueous sodium bicarbonate and further collecting the washed solution.
Add dilute hydrochloric acid for acidification, and then apply benzene to remove the free organic acid; Concentrate under reduced pressure to get rid of the benzene with the residue being the enriched product of caffeic acid.
Handling and Storage of Caffeic Acid:
Precautions for safe handling:
Advice on safe handling:
Work under hood.
Do not inhale substance/mixture.
Hygiene measures:
Immediately change contaminated clothing.
Apply preventive skin protection.
Wash hands and face after working with substance.
Conditions for safe storage, including any incompatibilities:
Storage conditions:
Tightly closed.
Keep locked up or in an area accessible only to qualified or authorized persons.
Storage class:
Storage class (TRGS 510): 11: Combustible Solids
Stability and Reactivity of Caffeic Acid:
Reactivity:
The following applies in general to flammable organic substances and mixtures: in correspondingly fine distribution, when whirled up a dust explosion potential may generally be assumed.
Chemical stability:
Caffeic acid is chemically stable under standard ambient conditions (room temperature).
Possibility of hazardous reactions:
Violent reactions possible with:
strong alkalis
Strong acids
Strong oxidizing agents
Conditions to avoid:
no information available
Incompatible materials:
No data available
First Aid Measures of Caffeic Acid:
General advice:
Show this material safety data sheet to the doctor in attendance.
After inhalation:
Fresh air.
Call in physician.
In case of skin contact:
Take off immediately all contaminated clothing.
Rinse skin with water/ shower.
Consult a physician.
After eye contact:
Rinse out with plenty of water.
Call in ophthalmologist.
Remove contact lenses.
After swallowing:
Immediately make victim drink water (two glasses at most).
Consult a physician.
Indication of any immediate medical attention and special treatment needed:
No data available
Firefighting Measures of Caffeic Acid:
Suitable extinguishing media:
Water Foam Carbon dioxide (CO2) Dry powder
Unsuitable extinguishing media:
For this substance/mixture no limitations of extinguishing agents are given.
Special hazards arising from the substance or mixture:
Carbon oxides
Combustible.
Development of hazardous combustion gases or vapours possible in the event of fire.
Advice for firefighters:
Stay in danger area only with self-contained breathing apparatus.
Prevent skin contact by keeping a safe distance or by wearing suitable protective clothing.
Further information:
Prevent fire extinguishing water from contaminating surface water or the ground water system
Accidental Release Measures of Caffeic Acid:
Personal precautions, protective equipment and emergency procedures:
Advice for non-emergency personnel:
Avoid inhalation of dusts.
Avoid substance contact.
Ensure adequate ventilation.
Evacuate the danger area, observe emergency procedures, consult an expert.
Environmental precautions:
Do not let product enter drains.
Methods and materials for containment and cleaning up:
Cover drains.
Collect, bind, and pump off spills.
Observe possible material restrictions.
Take up dry.
Dispose of properly.
Clean up affected area.
Avoid generation of dusts.
Exposure Controls/Personal Protection of Caffeic Acid:
Personal protective equipment:
Skin protection:
Full contact:
Material: Nitrile rubber
Minimum layer thickness: 0,11 mm
Break through time: 480 min
Material tested: KCL 741 Dermatril® L
Splash contact:
Material: Nitrile rubber
Minimum layer thickness: 0,11 mm
Break through time: 480 min
Material tested: KCL 741 Dermatril® L
Body Protection:
Protective clothing:
Respiratory protection required when dusts are generated.
Our recommendations on filtering respiratory protection are based on the following standards: DIN EN 143, DIN 14387 and other accompanying standards relating to the used respiratory protection system.
Recommended Filter type: Filter type P3
The entrepeneur has to ensure that maintenance, cleaning and testing of respiratory protective devices are carried out according to the instructions of the producer.
These measures have to be properly documented.
Control of environmental exposure
Do not let product enter drains.
Identifiers of Caffeic Acid:
CAS Number:
501-16-6
331-39-5 (non-specific)
Beilstein Reference: 1954563
ChEBI: CHEBI:16433
ChEMBL: ChEMBL145
ChemSpider: 600426
DrugBank: DB01880
ECHA InfoCard: 100.005.784
EC Number: 206-361-2
IUPHAR/BPS: 5155
KEGG: C01481
PubChem CID: 689043
UNII: U2S3A33KVM
CompTox Dashboard (EPA): DTXSID901316055 DTXSID5020231, DTXSID901316055
Linear Formula: (HO)2C6H3CH=CHCO2H
CAS Number: 331-39-5
Molecular Weight: 180.16
Beilstein: 1954563
EC Number: 206-361-2
MDL number: MFCD00004392
UNSPSC Code: 12352106
PubChem Substance ID: 24278290
NACRES: NA.77
CAS number: 331-39-5
ATP Competitive: N
Form: Tan crystalline solid
Hill Formula: C₉H₈O₄
Chemical formula: C₉H₈O₄
Reversible: N
Structure formula Image: Structure formula Image
Quality Level: MQ100
Properties of Caffeic Acid:
Chemical formula: C9H8O4
Molar mass: 180.16 g/mol
Density: 1.478 g/cm3
Melting point: 223 to 225 °C (433 to 437 °F; 496 to 498 K)
UV-vis (λmax): 327 nm and a shoulder at c. 295 nm in acidified methanol[1]
Quality Level: 200
Assay: ≥98.0% (HPLC)
form: powder
mp: 211-213 °C (dec.) (lit.)
solubility: ethanol: 50 mg/mL
SMILES string: OC(=O)\C=C\c1ccc(O)c(O)c1
InChI: 1S/C9H8O4/c10-7-3-1-6(5-8(7)11)2-4-9(12)13/h1-5,10-11H,(H,12,13)/b4-2+
InChI key: QAIPRVGONGVQAS-DUXPYHPUSA-N
Molecular Weight: 180.16 g/mol
XLogP3: 1.2
Hydrogen Bond Donor Count: 3
Hydrogen Bond Acceptor Count: 4
Rotatable Bond Count: 2
Exact Mass: 180.04225873 g/mol
Monoisotopic Mass: 180.04225873 g/mol
Topological Polar Surface Area: 77.8Ų
Heavy Atom Count: 13
Complexity: 212
Isotope Atom Count:
0Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 1
Undefined Bond Stereocenter Count: 0
Covalently-Bonded Unit Count: 1
Compound Is Canonicalized: Yes
Specifications of Caffeic Acid:
Catalog Number: ZXB-06-102
CAS Number: 331-39-5
Synonyms: 3,4-Dihydroxycinnamic acid
Formula: C9H8O4
Molecular Weight: 180.16
Storage: RT
PubChem Chemical ID: 689043
Related compounds of Caffeic Acid:
Chlorogenic acid
Cichoric acid
Coumaric acid
Quinic acid
Names of Caffeic Acid:
IUPAC names:
3-(3,4-Dihydroxyphenyl)-2-propenoic acid
3,4-Dihydroxycinnamic acid
trans-Caffeate
3,4-Dihydroxy-trans-cinnamate
(E)-3-(3,4-dihydroxyphenyl)-2-propenoic acid
3,4-Dihydroxybenzeneacrylicacid
3-(3,4-Dihydroxyphenyl)-2-propenoic acid
Preferred IUPAC name:
(2E)-3-(3,4-Dihydroxyphenyl)prop-2-enoic acid
MeSH Entry Terms of Caffeic Acid:
3,4-dihydroxycinnamic acid
caffeic acid
caffeic acid, (E)-isomer
caffeic acid, (Z)-isomer
caffeic acid, monosodium salt
cis-caffeic acid
sodium caffeate
trans-caffeic acid
