Caffeic acid

(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoic acid

C9H8O4 (180.0422568)


Caffeic acid is a hydroxycinnamic acid that is cinnamic acid in which the phenyl ring is substituted by hydroxy groups at positions 3 and 4. It exists in cis and trans forms; the latter is the more common. It has a role as a plant metabolite, an EC 1.13.11.33 (arachidonate 15-lipoxygenase) inhibitor, an EC 2.5.1.18 (glutathione transferase) inhibitor, an EC 1.13.11.34 (arachidonate 5-lipoxygenase) inhibitor, an antioxidant and an EC 3.5.1.98 (histone deacetylase) inhibitor. It is a hydroxycinnamic acid and a member of catechols. Caffeic Acid is a natural product found in Pavetta indica, Eupatorium cannabinum, and other organisms with data available. Caffeic Acid is an orally bioavailable, hydroxycinnamic acid derivative and polyphenol, with potential anti-oxidant, anti-inflammatory, and antineoplastic activities. Upon administration, caffeic acid acts as an antioxidant and prevents oxidative stress, thereby preventing DNA damage induced by free radicals. Caffeic acid targets and inhibits the histone demethylase (HDM) oncoprotein gene amplified in squamous cell carcinoma 1 (GASC1; JMJD2C; KDM4C) and inhibits cancer cell proliferation. GASC1, a member of the KDM4 subgroup of Jumonji (Jmj) domain-containing proteins, demethylates trimethylated lysine 9 and lysine 36 on histone H3 (H3K9 and H3K36), and plays a key role in tumor cell development. Caffeic acid is a metabolite found in or produced by Saccharomyces cerevisiae. See also: Black Cohosh (part of); Arctium lappa Root (part of); Comfrey Leaf (part of) ... View More ... 3,4-Dihydroxy-trans-cinnamate, also known as trans-Caffeate, is a polyphenol present in normal human urine positively correlated to coffee consumption and influenced by the dietary intake of diverse types of food (PMID:16870009). trans-Caffeic acid is found in many foods, some of which are flaxseed, cereal and cereal products, common grape, fruits, and common sage. It is also found in wine and coffee in free and conjugated forms. Caffeic acid (CAS: 331-39-5) is a polyphenol present in normal human urine positively correlated to coffee consumption and influenced by the dietary intake of diverse types of food (PMID:16870009). Caffeic acid has been found to be a microbial metabolite of Escherichia (PMID: 28396925). Caffeic acid. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=331-39-5 (retrieved 2024-06-28) (CAS RN: 331-39-5). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). Caffeic acid is an inhibitor of both TRPV1 ion channel and 5-Lipoxygenase (5-LO). Caffeic acid is an inhibitor of both TRPV1 ion channel and 5-Lipoxygenase (5-LO). Caffeic acid is an inhibitor of both TRPV1 ion channel and 5-Lipoxygenase (5-LO).

   

cis-Caffeic acid

(2Z)-3-(3,4-Dihydroxyphenyl)-2-propenoic acid

C9H8O4 (180.0422568)


Caffeic acid, also known as caffeate, belongs to the class of organic compounds known as hydroxycinnamic acids. Hydroxycinnamic acids are compounds containing an cinnamic acid where the benzene ring is hydroxylated. Caffeic acid exists in all living species, ranging from bacteria to humans. It is the precursor to ferulic acid, coniferyl alcohol, and sinapyl alcohol, all of which are significant building blocks in lignin. Outside of the human body, caffeic acid has been detected, but not quantified in fats and oils and nuts. Caffeic acid is formally rated as a possible carcinogen (by IARC 2B) and is also a potentially toxic compound. 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. It occurs at high levels in black chokeberry (141 mg per 100 g) and in fairly high level in lingonberry (6 mg per 100 g). D020011 - Protective Agents > D000975 - Antioxidants Found in olive oil, peanuts and other plant sources Caffeic acid is an inhibitor of both TRPV1 ion channel and 5-Lipoxygenase (5-LO). Caffeic acid is an inhibitor of both TRPV1 ion channel and 5-Lipoxygenase (5-LO). Caffeic acid is an inhibitor of both TRPV1 ion channel and 5-Lipoxygenase (5-LO).

   

Caffeate

(2Z)-3-(3,4-dihydroxyphenyl)prop-2-enoic acid

C9H8O4 (180.0422568)


D020011 - Protective Agents > D000975 - Antioxidants KEIO_ID C107 Caffeic acid is an inhibitor of both TRPV1 ion channel and 5-Lipoxygenase (5-LO). Caffeic acid is an inhibitor of both TRPV1 ion channel and 5-Lipoxygenase (5-LO). Caffeic acid is an inhibitor of both TRPV1 ion channel and 5-Lipoxygenase (5-LO).

   

Caffeic Acid

3,4-dihydroxy cinnamic acid

C9H8O4 (180.0422568)


A hydroxycinnamic acid that is cinnamic acid in which the phenyl ring is substituted by hydroxy groups at positions 3 and 4. It exists in cis and trans forms; the latter is the more common. 3,4-dihydroxycinnamic acid, also known as caffeic acid or trans-caffeate, is a member of the class of compounds known as hydroxycinnamic acids. Hydroxycinnamic acids are compounds containing an cinnamic acid where the benzene ring is hydroxylated. 3,4-dihydroxycinnamic acid is slightly soluble (in water) and a weakly acidic compound (based on its pKa). 3,4-dihydroxycinnamic acid can be found in fats and oils and nuts, which makes 3,4-dihydroxycinnamic acid a potential biomarker for the consumption of these food products. 3,4-dihydroxycinnamic acid exists in all eukaryotes, ranging from yeast to humans. Caffeic acid is an organic compound that is classified as a hydroxycinnamic acid. This yellow solid consists of both phenolic and acrylic functional groups. It is found in all plants because it is a key intermediate in the biosynthesis of lignin, one of the principal components of plant biomass and its residues . Caffeic acid is a polyphenol present in normal human urine positively correlated to coffee consumption and influenced by the dietary intake of diverse types of food. (PMID:16870009) [HMDB]. Caffeic acid is found in many foods, some of which are cardoon, coriander, common persimmon, and irish moss. D020011 - Protective Agents > D000975 - Antioxidants Annotation level-2 CONFIDENCE standard compound; INTERNAL_ID 167 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.412 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.403 Caffeic acid is an inhibitor of both TRPV1 ion channel and 5-Lipoxygenase (5-LO). Caffeic acid is an inhibitor of both TRPV1 ion channel and 5-Lipoxygenase (5-LO). Caffeic acid is an inhibitor of both TRPV1 ion channel and 5-Lipoxygenase (5-LO).

   

AI3-63211

InChI=1\C9H8O4\c10-7-3-1-6(5-8(7)11)2-4-9(12)13\h1-5,10-11H,(H,12,13)\b4-2

C9H8O4 (180.0422568)


D020011 - Protective Agents > D000975 - Antioxidants Caffeic acid is an inhibitor of both TRPV1 ion channel and 5-Lipoxygenase (5-LO). Caffeic acid is an inhibitor of both TRPV1 ion channel and 5-Lipoxygenase (5-LO). Caffeic acid is an inhibitor of both TRPV1 ion channel and 5-Lipoxygenase (5-LO).

   

3-[3-(3,4-dihydroxyphenyl)-2-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]prop-2-enoic acid

3-[3-(3,4-dihydroxyphenyl)-2-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]prop-2-enoic acid

C18H16O7 (344.0895986)


   

6-methyloxane-3,4-diol

6-methyloxane-3,4-diol

C6H12O3 (132.0786402)


   

(1as,7ar,7bs)-3,3,5-trimethyl-6-oxo-1h,1ah,2h,4h,7h,7ah-cyclopropa[e]azulene-7b-carboxylic acid

(1as,7ar,7bs)-3,3,5-trimethyl-6-oxo-1h,1ah,2h,4h,7h,7ah-cyclopropa[e]azulene-7b-carboxylic acid

C15H20O3 (248.14123700000002)


   

(3r,4r,6r)-6-methyloxane-3,4-diol

(3r,4r,6r)-6-methyloxane-3,4-diol

C6H12O3 (132.0786402)


   

(3r,4s,12s,13s)-3,12-dimethyl-2,11-dioxatricyclo[12.4.0.0⁵,¹⁰]octadeca-1(18),5,7,9,14,16-hexaene-4,6,13,15-tetrol

(3r,4s,12s,13s)-3,12-dimethyl-2,11-dioxatricyclo[12.4.0.0⁵,¹⁰]octadeca-1(18),5,7,9,14,16-hexaene-4,6,13,15-tetrol

C18H20O6 (332.125982)


   

(3s,4s,6r)-6-methyloxane-3,4-diol

(3s,4s,6r)-6-methyloxane-3,4-diol

C6H12O3 (132.0786402)


   

3,12-dimethyl-2,11-dioxatricyclo[12.4.0.0⁵,¹⁰]octadeca-1(18),5,7,9,14,16-hexaene-4,6,13,15-tetrol

3,12-dimethyl-2,11-dioxatricyclo[12.4.0.0⁵,¹⁰]octadeca-1(18),5,7,9,14,16-hexaene-4,6,13,15-tetrol

C18H20O6 (332.125982)


   

(2r,3r,4r,5s)-4,5-dihydroxy-2-methyloxan-3-yl (2z)-but-2-enoate

(2r,3r,4r,5s)-4,5-dihydroxy-2-methyloxan-3-yl (2z)-but-2-enoate

C10H16O5 (216.0997686)


   

(2s,3r,4s,5s)-4,5-dihydroxy-2-methyloxan-3-yl (2z)-but-2-enoate

(2s,3r,4s,5s)-4,5-dihydroxy-2-methyloxan-3-yl (2z)-but-2-enoate

C10H16O5 (216.0997686)


   

3,3,5-trimethyl-6-oxo-1h,1ah,2h,4h,7h,7ah-cyclopropa[e]azulene-7b-carboxylic acid

3,3,5-trimethyl-6-oxo-1h,1ah,2h,4h,7h,7ah-cyclopropa[e]azulene-7b-carboxylic acid

C15H20O3 (248.14123700000002)


   

(3s,4r,6r)-6-methyloxane-3,4-diol

(3s,4r,6r)-6-methyloxane-3,4-diol

C6H12O3 (132.0786402)


   

4,5-dihydroxy-2-methyloxan-3-yl but-2-enoate

4,5-dihydroxy-2-methyloxan-3-yl but-2-enoate

C10H16O5 (216.0997686)


   

(2e)-3-[(2r,3r)-3-(3,4-dihydroxyphenyl)-2-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]prop-2-enoic acid

(2e)-3-[(2r,3r)-3-(3,4-dihydroxyphenyl)-2-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]prop-2-enoic acid

C18H16O7 (344.0895986)