trans-caffeic acid
(E)-3-(3,4-dihydroxyphenyl)-2-propenoic acid
 
Notes:
Widespread in plants, free and as glycosides. Present in fruits, cereals, wine and coffee in free and conjugated forms 3,4-Dihydroxy-trans-cinnamate 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)
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CAS Number: 501-16-6Picture of molecule3D/inchi
FDA UNII: U2S3A33KVM
Nikkaji Web: J309.143K
Beilstein Number: 2210883
MDL: MFCD00004392
XlogP3: 1.20 (est)
Molecular Weight: 180.15956000
Formula: C9 H8 O4
BioActivity Summary: listing
NMR Predictor: Predict (works with chrome or firefox)
Category: natural substances and extractives
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
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PubMed: Search
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Physical Properties:
Appearance: yellow crystals (est)
Assay: 95.00 to 100.00 % 
Food Chemicals Codex Listed: No
Boiling Point: 416.80 °C. @ 760.00 mm Hg (est)
Flash Point: 428.00 °F. TCC ( 220.00 °C. ) (est)
logP (o/w): 1.420 (est)
Soluble in:
 water, 5.407e+004 mg/L @ 25 °C (est)
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Organoleptic Properties:
 
Odor and/or flavor descriptions from others (if found).
 
 
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Cosmetic Information:
None found
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Suppliers:
Coompo
For experimental / research use only.
trans-Caffeic Acid from Plants ≥98%
Sigma-Aldrich
For experimental / research use only.
trans-Caffeic Acid
certified reference material, TraceCERT®
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Safety Information:
 
Hazards identification
 
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
 
Pictogram
 
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
Not determined
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
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Safety in Use Information:
Category: natural substances and extractives
Recommendation for trans-caffeic acid usage levels up to:
 not for fragrance use.
 
Recommendation for trans-caffeic acid flavor usage levels up to:
 not for flavor use.
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Safety References:
EPI System: View
AIDS Citations: Search
Cancer Citations: Search
Toxicology Citations: Search
EPA ACToR: Toxicology Data
EPA Substance Registry Services (SRS): Registry
Laboratory Chemical Safety Summary : 689043
National Institute of Allergy and Infectious Diseases: Data
WGK Germany: 3
 (E)-3-(3,4-dihydroxyphenyl)prop-2-enoic acid
Chemidplus: 0000501166
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References:
 (E)-3-(3,4-dihydroxyphenyl)prop-2-enoic acid
NIST Chemistry WebBook: Search Inchi
Pubchem (cid): 689043
Pubchem (sid): 134973965
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Other Information:
(IUPAC): Atomic Weights of the Elements 2011 (pdf)
Videos: The Periodic Table of Videos
tgsc: Atomic Weights use for this web site
(IUPAC): Periodic Table of the Elements
CHEBI: View
CHEMBL: View
Golm Metabolome Database: Search
KEGG (GenomeNet): C01197
HMDB (The Human Metabolome Database): HMDB03501
FooDB: FDB002559
VCF-Online: VCF Volatile Compounds in Food
ChemSpider: View
Wikipedia: View
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Potential Blenders and core components note
 
None Found
 
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Potential Uses:
None Found
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Occurrence (nature, food, other): note
 alfalfa
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 bean field bean
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 chamomile
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 cherry sweet cherry
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 chickpea
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 coffee
Search  PMC Picture
 dandelion
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 flax seed
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 grape fruit
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 pea
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 peanut
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 poppy opium poppy
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 sage
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 soybean
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 wine
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Synonyms:
(E)-caffeic acid
 caffeic acid, trans-
(E)-3-(3,4-dihydroxy-phenyl)-acrylic acid
(E)-3,4-dihydroxycinnamic acid
trans-3,4-dihydroxycinnamic acid
(2E)-3-(3,4-dihydroxyphenyl)-2-propenoic acid
(E)-3-(3,4-dihydroxyphenyl)-2-propenoic acid
(2E)-3-(3,4-dihydroxyphenyl)acrylic acid
(E)-3-(3,4-dihydroxyphenyl)acrylic acid
(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoic acid
(E)-3-(3,4-dihydroxyphenyl)prop-2-enoic acid
2-propenoic acid, 3-(3,4-dihydroxyphenyl)-, (2E)-
2-propenoic acid, 3-(3,4-dihydroxyphenyl)-, (E)-
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Articles:
PubMed: Antitubercular activity of Arctium lappa and Tussilago farfara extracts and constituents.
PubMed: Leaf Extract of Markhamia platycalyx: Polyphenolic Profile, Acute Toxicity, Anti-inflammatory, Hepatoprotective and in vitro Antioxidant Activities.
PubMed: [Chemical constituents from ethyl acetate extract of Artemisia rupestris].
PubMed: Biotransformation of 4,5-O-dicaffeoylquinic acid methyl ester by human intestinal flora and evaluation on their inhibition of NO production and antioxidant activity of the products.
PubMed: [Chemical constituents of the roots of Vaccinium bracteatum].
PubMed: trans-Caffeic acid stearyl ester from Paeonia suffruticosa inhibits melanin synthesis by cAMP-mediating down-regulation of α-melanocyte-stimulating hormone-stimulated melanogenesis signaling pathway in B16 cells.
PubMed: [Chemical constituents of Phymatopteris hastate and their antioxidant activity].
PubMed: Absorption, disposition, metabolism, and excretion of [3-(14)C]caffeic acid in rats.
PubMed: Melissa officinalis extract inhibits attachment of herpes simplex virus in vitro.
PubMed: Antioxidant, anti-glycation and anti-inflammatory activities of phenolic constituents from Cordia sinensis.
PubMed: [Studies on the chemical constituents from the roots of Kalopanax septemlobus].
PubMed: The blue anthocyanin pigments from the blue flowers of Heliophila coronopifolia L. (Brassicaceae).
PubMed: Profiling of resveratrol oligomers, important stress metabolites, accumulating in the leaves of hybrid Vitis vinifera (Merzling × Teroldego) genotypes infected with Plasmopara viticola.
PubMed: Relationship between nonvolatile composition and sensory properties of premium Spanish red wines and their correlation to quality perception.
PubMed: Identification of new derivatives of 2-S-glutathionylcaftaric acid in aged white wines by HPLC-DAD-ESI-MS(n).
PubMed: [Two new phenolic acids from Drynariae rhizoma].
PubMed: Depsides and other polar constituents from Origanum dictamnus L. and their in vitro antimicrobial activity in clinical strains.
PubMed: Enantioselective synthesis and antioxidant activity of 3-(3,4-dihydroxyphenyl)-glyceric acid--basic monomeric moiety of a biologically active polyether from Symphytum asperum and S. caucasicum.
PubMed: [HPLC fingerprint of chemical constituents of Flos Farfarae].
PubMed: [Studies on chemical constituents of Evodia rutaecarpa].
PubMed: Analyzing effects of extra-virgin olive oil polyphenols on breast cancer-associated fatty acid synthase protein expression using reverse-phase protein microarrays.
PubMed: Anemonin, from Clematis crassifolia, potent and selective inducible nitric oxide synthase inhibitor.
PubMed: [Study on the terpenoids of chemical constituents of Buddleja purdomii (II)].
PubMed: Bioactive constituents from Chinese natural medicines. XXVI. Chemical structures and hepatoprotective effects of constituents from roots of Rhodiola sachalinensis.
PubMed: Occurrence of N-phenylpropenoyl-L-amino acid amides in different herbal drugs and their influence on human keratinocytes, on human liver cells and on adhesion of Helicobacter pylori to the human stomach.
PubMed: Genes and enzymes involved in caffeic acid biosynthesis in the actinomycete Saccharothrix espanaensis.
PubMed: [Phenolic compounds isolated from rhizoma of Aster tataricus].
PubMed: NMR assignments and single-crystal X-ray diffraction analysis of deoxyloganic acid.
PubMed: Hydroxycinnamic acids do not prevent aortic atherosclerosis in hypercholesterolemic golden Syrian hamsters.
PubMed: Neuroprotective phenylpropanoid esters of rhamnose isolated from roots of Scrophularia buergeriana.
PubMed: Spanish sparkling wines (Cavas) as inhibitors of in vitro human low-density lipoprotein oxidation.
PubMed: Metabolites of orally administered Perilla frutescens extract in rats and humans.
PubMed: Metabolism of rosmarinic acid in rats.
PubMed: Two novel compounds from Paeonia suffructicosa.
PubMed: Caffeic acid and glycerol are constituents of the suberin layers in green cotton fibres.
PubMed: [Structure of swertiamacroside from Swertia macrosperma C.B. Clark].
PubMed: Formation of trans-caffeoyl-CoA from trans-4-coumaroyl-CoA by Zn2+-dependent enzymes in cultured plant cells and its activation by an elicitor-induced pH shift.
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