4-Coumaric acid (HCID 322)

Names & identifiers

Preferred name: 4-Coumaric acid
IUPAC: 3-(4-hydroxyphenyl)prop-2-enoic acid
English name: 4-Hydroxycinnamic acid
Molecular formula: C9H8O3
Molecular weight: 164.16

Names & synonyms

DTXSID6064660CHEBI:360903-(4-hydroxyphenyl)prop-2-enoic acidRefChem:1070546DTXCID10476054-Coumaric acidp-Hydroxycinnamic acidp-Hydroxy-cinnamic acid4-trans-4-Hydroxycinnamic acidparahydroxycinnamic acidp-hydroxy cinnamic acidAlkaline ceramidase

Show more names

4-Hydroxycinnamic acidTRANS-P-COUMARIC ACIDTRANS-4-COUMARIC ACIDP-CUMARIC ACIDPHCA3-(4-HYDROXYPHENYL)ACRYLIC ACID3-(4-Hydroxyphenyl)-2-propenoic acidpara-Coumaric acidTRANS-P-CUMARIC ACID

2-Propenoic acid, 3-(4-hydroxyphenyl)-, (2Z)-4hydroxycinnamic acid4- hydroxycinnamic acid4-hy droxycinnamic acid4-hydroxy-cinnamic acidEnamine_005378p-Coumaric acid (NIST)Epitope ID:116879

Database identifiers

CAS: 7400-08-0
PubChem CID: 322
DTXSID: DTXSID6064660
EC Number: 231-000-0

Properties

Computed structural properties

XLogP: 1.5
Topological polar surface area: 57.5 Å²
Hydrogen bond donors: 2
Hydrogen bond acceptors: 3
Rotatable bonds: 2
Heavy atoms: 12
Formal charge: 0
Complexity: 178

Physicochemical properties

Melting point: 214 °C · 214 °C (dec.)(lit.)
Boiling point: 251.61 °C · 251.61°C (rough estimate)
Density: 1.2132 · 1.2132 (rough estimate)
refractive index: 1.538 · 1.5380 (estimate)
storage temp.: 30 °C · Store below +30°C.
solubility: Acetone (Slightly), Chloroform (Slightly), Methanol (Slightly)
form: Solid
pka: 4.65 · 4.65±0.10(Predicted)
color: White to Off-White
biological source: rabbit
Stability: Light Sensitive
Cosmetics Ingredients Functions: SKIN CONDITIONING
InChI: InChI=1S/C9H8O3/c10-8-4-1-7(2-5-8)3-6-9(11)12/h1-6,10H,(H,11,12)
InChIKey: NGSWKAQJJWESNS-UHFFFAOYSA-N
SMILES: C(O)(=O)C=CC1=CC=C(O)C=C1
LogP: 1.79 · 1.790
CAS DataBase Reference: 7400 · 7400-08-0(CAS DataBase Reference)
FDA UNII: 9 D1EU3J · IBS9D1EU3J
NIST Chemistry Reference: 2 · 2-Propenoic acid, 3-(4-hydroxyphenyl)-(7400-08-0)
EPA Substance Registry System: p-Hydroxycinnamic acid (7400-08-0)
UNSPSC Code: 12352203 · 12352203
NACRES: 41 · NA.41
Symbol(GHS): 7 · GHS07
Signal word: Warning
Hazard statements: 315 · H315-H319-H335
Precautionary statements: 261 · P261-P264-P271-P280-P302+P352-P305+P351+P338
target organs: Respiratory system
Hazard Codes: Xi
Risk Statements: 36 · 36/37/38
Safety Statements: 26 · 26-36-36/37/39-22
WGK Germany: 2 · 2
RTECS: 9095000 · GD9095000
TSCA: TSCA listed
HS Code: 2918 · 2918 29 00
Storage Class: 11 · 11 - Combustible Solids
Hazard Classifications: 2 Skin · Eye Irrit. 2Skin Irrit. 2STOT SE 3
REACH Registrations: Active

Safety & regulation

Safety data

wgk: 2
tsca: TSCA listed
rtecs: GD9095000
hs_code: 2918 29 00
risk_code: 36/37/38
Signal word: Warning
Symbol(GHS): GHS07
hazard_code: Xi
safety_code: 26-36-36/37/39-22
Storage Class: 11 - Combustible Solids
target organs: Respiratory system
Hazard statements: H315-H319-H335
REACH Registrations: Active
Hazard Classifications: Eye Irrit. 2Skin Irrit. 2STOT SE 3
Precautionary statements: P261-P264-P271-P280-P302+P352-P305+P351+P338

Chemistry & industry

Applications · 1 item

Uses4-Hydroxycinnamic acid is the hydroxy derivative of Cinnamic Acid with antioxidant properties. It is a is a major component of lignocellulose. Studies suggest that 4-Hydroxycinnamic acid may reduce the risk of cancer by reducing the formation of carcinogenic nitrosamines. A recent study reports that 4-Hydroxycinnamic acid may act as a chemical castrator in bees by altering the epression of genes required for ovary development. This compound is common in pollen a major constituent of the worker bee diet, but it is not found in queen bees'royal jelly.

Upstream & downstream products

Upstream raw materials

Nordihydroguaiaretic acid L-Phenylalanine

Downstream products

Ciprofibrate Cyclohexanepropionic acid Methyl 3-(4-hydroxyphenyl)propionate 3-Amino-3-(4-hydroxyphenyl)propanoic acid 4-Hydroxy-β-nitrostyrene BOLTON-HUNTER REAGENT N-(p-Coumaroyl) Serotonin Methyl p-coumarate 3-(4-Hydroxyphenyl)propenoic acid benzyl ester Methyl 4-prenyloxycinnamate 2-Propenoic acid, 3-[4-(decyloxy)phenyl]-

Suppliers50 total

T&W GROUP021-61551611 13296011611 · [email protected]

金华市佰康生物工程有限公司0573-15557365800 15557365800

北京安司莫森技术有限公司010-82954736 13391601435 · [email protected]

韶远科技（上海）有限公司021-50795510 4000665055 · [email protected]

上海迈瑞尔生化科技有限公司4006356688 18621169109 · [email protected]

Additional notes

DefinitionChEBI: 4-coumaric acid is a coumaric acid in which the hydroxy substituent is located at C-4 of the phenyl ring. It has a role as a plant metabolite. It is a conjugate acid of a 4-coumarate.