3-(3,4-Dihydroxyphenyl)Prop-2-Enoic Acid

HCID 2518
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Basic information

CAS
331-39-5
Standard SMILES
O=C(O)C=Cc1ccc(O)c(O)c1
InChIKey
QAIPRVGONGVQAS-UHFFFAOYSA-N
Molecular formula
C9H8O4
Average molar mass
180.16 g/mol
Monoisotopic mass
180.04225874

Overview

QAIPRVGONGVQAS-UHFFFAOYSA-N has been reported in Salvia miltiorrhiza, Acanthospermum australe, and other organisms with data available.

Names & identifiers

Preferred name
3-(3,4-Dihydroxyphenyl)Prop-2-Enoic Acid
IUPAC
3-(3,4-dihydroxyphenyl)prop-2-enoic acid
English name
Caffeic acid
Molecular formula
C9H8O4
Molecular weight
180.16

Names & synonyms

3-(3,4-dihydroxyphenyl)prop-2-enoic acidRefChem:1066648MFCD000043923,4-dihydroxycinnamic acid (caffeic acid)3,4-Dihydroxycinnamic acid, predominantly transSpectrum_001686SpecPlus_000528Prestwick0_000902Prestwick1_000902Spectrum2_001612Spectrum4_0016943,4-dihydroxy cinnamic acid
Show more names
3,4-DIHYDROXYCINNAMIC ACID(E)-3-(3,4-Dihydroxyphenyl)acrylic acidCaffeicCAFFIC ACID31-39-53-(3,4-DIHYDROXYPHENYL)ACRYLIC ACIDCaffeic acid 04-(2’-carboxyvinyl)-1,2-dihydroxybenzeneβ-(3NSC 623438
SCHEMBL23359KBioGR_001988KBioSS_002166orb322303DivK1c_006624SPBio_001643SPBio_002943orb1304995

Database identifiers

CAS
331-39-5
PubChem CID
2518
DTXSID
DTXSID5020231
ChEMBL
CHEMBL3181904

Properties

Computed structural properties

XLogP
1.2
Topological polar surface area
77.8 Ų
Hydrogen bond donors
3
Hydrogen bond acceptors
4
Rotatable bonds
2
Heavy atoms
13

Experimental & physicochemical properties

Chemical ClassesStimulant

Physicochemical properties

Melting point
211 · 211-213 °C (dec.) (lit.)
Boiling point
272.96 °C · 272.96°C (rough estimate)
Density
1.2933 · 1.2933 (rough estimate)
refractive index
1.45 · 1.4500 (estimate)
storage temp.
2 · 2-8°C
solubility
50 mg/mL · ethanol: 50 mg/mL

Safety & regulation

Safety data

PPE
Eyeshields, Gloves, type P3 (EN 143) respirator cartridges
wgk
3
rtecs
GD8950000
hs_code
29182990
risk_code
36/37/38-40-63-68
Signal word
Warning

Chemistry & industry

Applications · 7 items

Uses1. Reagents for Organic Synthesis. 2. Intermediate of caffeic acid; can be used in organic synthesis. 3. Used for Biochemical studies.

DescriptionCaffeic acid is abundant in the whole plant of Solidago decurrens Lour. (Yi Zhi Huang Hua), fruit of Crataegus pinnatifida Bge. var. major N.E.Br. (Shan Li Hong), Salix myrtillacea Anderss. (Po Liu), rhizome of Cimicifuga foetida L., rhizome of Polypodiaceae Polypodium vulgare L. (Ou Ya Shui Long Gu), peel of Rutaceae Citrus limonum (Ning Meng), the whole plant of Polygonaceae Polygonum aviculare L. (Pian Xu), root of Valeriana officinalis L. (Xie Cao), the whole plant of Thymus mongolicus Ronn (She Xiang), leaves of Eucommia ulmoides (Du Zhong), and other herbal plants. It is a kind of polyhydroxy styrene acid, with the general chemical properties of phenolic acid. It is easily oxidized for the reason of the unsaturated double bonds, particularly unstable in alkaline solutionCaffeic 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.

DescriptionCaffeic acid is an inhibitor of 5-LO with an IC50 value of 3.7-72 μM and 12-LO with an IC50 value of 5.1-30 μM.

UsesCaffeic Acid is a constituent of plants, probably occurs in plants only in conjugated forms. Caffeic acid is found in all plants because it is a key intermediate in the biosynthesis of lignin, one of the principal sources of biomass. Caffeic acid is one of the main natural phenols in argan oi.

UsesCaffeic 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. It has also been used to determine its antioxidant activity by various assay methods.

Usesantineoplastic, PGE2 synthase inhibitor, PK inhibitor

General DescriptionYellow prisms or plates (from chloroform or ligroin) or pale yellow granules. Alkaline solutions turn from yellow to orange.

Upstream & downstream products

Suppliers101 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]
北京华美互利生物化工010-56205725 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
成都健腾生物技术有限公司028-85159085 · [email protected]
Additional notes · 1 item

DefinitionChEBI: 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.

Related reactions

9 records
New reaction record

Compound notes

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