(2E)-3-(2-hydroxyphenyl)prop-2-enoic acid

• ChemBase ID: 1426
• Molecular Formular: C9H8O3
• Molecular Mass: 164.15802
• Monoisotopic Mass: 164.04734412
• SMILES: C(=C\c1ccccc1O)/C(=O)O
• Canonical SMILES: OC(=O)/C=C/c1ccccc1O
• InChI: InChI=1S/C9H8O3/c10-8-4-2-1-3-7(8)5-6-9(11)12/h1-6,10H,(H,11,12)/b6-5+
• InChIKey: PMOWTIHVNWZYFI-AATRIKPKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2E)-3-(2-hydroxyphenyl)prop-2-enoic acid; 3-(2-hydroxyphenyl)prop-2-enoic acid
• IUPAC Traditional name: O-coumaric acid; trans-2-hydroxycinnamic acid
• Synonyms: trans-2-Hydroxycinnamic acid; (E)-3-(2-hydroxyphenyl)acrylic acid; O-Coumaric Acid; 3-(2-hydroxyphenyl)acrylic acid; 2-Hydroxycinnamic acid; 2-Hydroxycinnamate; 2-Coumaric acid; 2-Coumarate; (e)-o-hydroxycinnamic acid; (E)-3-(2-Hydroxyphenyl)-2-propenoic acid; (2E)-3-(2-Hydroxyphenyl)-2-propenoic acid; (2E)-3-(2-HYDROXYPHENYL)ACRYLIC ACID; (2E)-3-(2-hydroxyphenyl)prop-2-enoic acid; 3-(2-hydroxyphenyl)prop-2-enoic acid; O-hydroxy-trans-cinnamic acid; O-hydroxycinnamic acid; Ortho-hydroxycinnamic acid; trans-2-Hydroxycinnamate; Trans-o-coumaric acid; Trans-o-hydroxycinnamic acid; trans-2-hydroxycinnamic acid; 2-Hydroxycinnamic acid; o-COUMARIC ACID; ortho-coumaric acid; trans-2-Hydroxycinnamic acid; 2-Hydroxycinnamic acid, predominantly trans; 反式-2-羟基肉桂酸; 反式-2-羟基肉桂酸; 邻香豆酸; 2-羟基肉桂酸，主要为反式

Database IDs

• CAS Number: 583-17-5; 614-60-8
• EC Number: 210-386-4
• MDL Number: MFCD00004379
• Beilstein Number: 1100900
• PubChem SID: 24856991; 24895158; 160964886; 46505688
• PubChem CID: 637540
• Chemspider ID: 553146
• Wikipedia Title: O-Coumaric_acid

CALCULATED PROPERTIES

JChem

• Acid pKa: 4.0376344
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 0.35907778
• LogD (pH = 7.4): -1.3093433
• Log P: 1.832521
• Molar Refractivity: 45.0408 cm^3
• Polarizability: 16.809118 Å^3
• Polar Surface Area: 57.53 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 1.9
• LOG S: -2.15
• Solubility (Water): 1.15e+00 g/l

PROPERTIES

Physical Property

• Melting Point: ~210 °C (dec.); 217 °C (dec.)(lit.); 217°C; 217(dec.)°C; ca 210°C dec.

Safety Information

• Storage Condition: Room Temperature (15-30°C)
• Storage Warning: Toxic/Irritant
• RTECS: GD9090000
• European Hazard Symbols: Irritant (Xi); Harmful (Xn)
• UN Number: 2811
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 3
• Risk Statements: 22-36/37/38; 36/37/38
• Safety Statements: 26; 26-37
• TSCA Listed: 是
• GHS Pictograms: GHS06; GHS07
• GHS Signal Word: Danger
• GHS Hazard statements: H301-H315-H319-H335; H315-H319-H335
• GHS Precautionary statements: P261-P301 + P310-P305 + P351 + P338; P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves
• RID/ADR: UN 2811 6.1/PG 3

Product Information

• Purity: ~97%; ≥97.0% (HPLC); 97%; 98+%
• Grade: purum
• Linear Formula: HOC6H4CH=CHCO2H
• Empirical Formula (Hill Notation): C9H8O3
• Classification: Genuine Natural Compounds

DETAILS

MP Biomedicals - 05206912

MP Biomedicals Rare Chemical collection

MP Biomedicals - 02150712

Crystalline
Purity: ~97%
Predominantly trans-isomer.

DrugBank - DB01650

Drug information: experimental

Apollo Scientific Ltd - OR40640

Mixture of cis/trans isomers

Sigma Aldrich - H22809

Packaging
25 g in poly bottle
5 g in glass bottle

REFERENCES

• Coumarin precursor. 2-Hydroxycinnamoyl has been employed as a photoremovable protecting group for amines. The amide can be formed by DCC coupling with the acid; the amine can be recovered in high yield after irradiation, with formation of coumarin: Chem. Pharm. Bull., 45, 715 (1997).