Basic information
- CAS
583-17-5- Standard SMILES
O=C(O)/C=C/c1ccccc1O- InChIKey
PMOWTIHVNWZYFI-AATRIKPKSA-N- Molecular formula
- C9H8O3
- Average molar mass
- 164.16 g/mol
- Monoisotopic mass
- 164.04734412
Overview
2-coumaric acid is a monohydroxycinnamic acid in which the hydroxy substituent is located at C-2 of the phenyl ring. It has a role as a plant metabolite. It is a conjugate acid of a 2-coumarate.
Names & identifiers
- Preferred name
- O-Coumaric Acid
- IUPAC
- (E)-3-(2-hydroxyphenyl)prop-2-enoic acid
- English name
- 2-HYDROXYCINNAMIC ACID
- Molecular formula
- C9H8O3
- Molecular weight
- 164.16
Names & synonyms
2-Hydroxycinnamic acido-Coumaric acid583-17-53-(2-hydroxyphenyl)acrylic acid(E)-3-(2-hydroxyphenyl)prop-2-enoic acid(E)-2-hydroxycinnamic acid2-Propenoic acid, 3-(2-hydroxyphenyl)-2S0H1PX3LMRefChem:25837209-500-5614-60-8trans-2-Hydroxycinnamic acid
Show more names
2-hydroxycinnamic acid, predominantly transO-HYDROXYCINNAMIC ACIDO-CUMARIC ACIDCOUMARIC ACID,2-2-HydroxyzimtsureORTHO-COUMARICACIDCoumaric Acid2-(P)
trans-o-Coumaric acid2-Coumaric acidtrans-o-Hydroxycinnamic acid2-Coumarate2-Hydroxycinnamate(E)-o-Hydroxycinnamic acid(2E)-3-(2-hydroxyphenyl)prop-2-enoic acidtrans-2-Hydroxycinnamate
Database identifiers
- CAS
583-17-5、614-60-8- PubChem CID
- 637540
- DTXSID
DTXSID10883240- ChEMBL
CHEMBL52564- ChEBI
CHEBI:18176- UNII
- 23AU5FZB9C
- EC Number
- 209-500-5、210-386-4
- Nikkaji
- J55.415D、J7.442J
Properties
Computed structural properties
- XLogP
- 1.5
- Topological polar surface area
- 57.5 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 2
- Heavy atoms
- 12
- Formal charge
- 0
- Complexity
- 186
Experimental & physicochemical properties
Chemical ClassesOther Classes -> Organic Acids
DrugsPharmaceuticals -> Listed in ZINC15
SpringerMaterials PropertiesCrystal structure
LogP0.62
Food AdditivesFLAVORING AGENT OR ADJUVANT -> FDA Substance added to food
Physical Description
Off-white or beige powder; [Acros Organics MSDS]
Solid
Collision Cross Section124.1 Ų [M+H-H2O]+ [CCS Type: DT; Method: single field calibrated with Agilent tune mix (Agilent)]
Physicochemical properties
- Melting point
- 217 °C · 217 °C (dec.)(lit.)
- Boiling point
- 231.61 °C · 231.61°C (rough estimate)
- Density
- 1.1403 · 1.1403 (rough estimate)
- refractive index
- 1.45 · 1.4500 (estimate)
- FEMA
- 4700 · 4700 | O-TRANS-COUMARIC ACID
- storage temp.
- Inert atmosphere,Room Temperature
- solubility
- DMSO (Slightly), Ethyl Acetate (Slightly)
- form
- Solid
- pka
- 1 · pK1:4.614 (25°C)
- color
- Off-White
- Water Solubility
- slightly soluble in water
- BRN
- 1100900 · 1100900
- 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
- SMILES
- OC(=O)\C=C\c1ccccc1O
- LogP
- 2.43 · 2.43
- CAS DataBase Reference
- 614 · 614-60-8(CAS DataBase Reference)
- Substances Added to Food (formerly EAFUS)
- O-TRANS-COUMARIC ACID
- EWG's Food Scores
- 1 · 1
- FDA UNII
- 23 AU5FZB9C · 23AU5FZB9C
- EPA Substance Registry System
- (E)-o-Hydroxycinnamic acid (614-60-8)
- UNSPSC Code
- 41116107 · 41116107
- NACRES
- 24 · NA.24
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 302 · H302-H315-H319-H335
- Precautionary statements
- 261 · P261-P264-P270-P301+P312-P302+P352-P305+P351+P338
- target organs
- Respiratory system
- PPE
- 95 · dust mask type N95 (US), Eyeshields, Faceshields, Gloves
- Hazard Codes
- Xn,Xi
- Risk Statements
- 22 · 22-36/37/38
- Safety Statements
- 26 · 26-24/25-36
- RIDADR
- 2811 · UN 2811 6.1/PG 3
- WGK Germany
- 3 · 3
- RTECS
- 9090000 · GD9090000
- TSCA
- TSCA listed
- HS Code
- 2918.29 · 2918.29.7500
- HazardClass
- 6.1 · 6.1
- Storage Class
- 11 · 11 - Combustible Solids
- Hazard Classifications
- 4 OralEye · Acute Tox. 4 OralEye Irrit. 2Skin Irrit. 2STOT SE 3
- Limited Quantities
- 5 kg · 5.0 kg (11 lbs) (solid)
- Excepted Quantities
- Max Inner Pack (30g or 30ml) and Max Outer Pack (1Kg or 1L)
Safety & regulation
GHS classification
GHS Classification
This chemical does not meet GHS hazard criteria for 56.8% (104 of 183) of all reports.
Danger
H301 (26.2%): Toxic if swallowed [Danger Acute toxicity, oral]
P261, P264, P264+P265, P270, P271, P280, P301+P316, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 183 reports by companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory Information2-Hydroxycinnamic acid: Does not have an individual approval but may be used under an appropriate group standard
Hazards SummaryAn irritant; [Acros Organics MSDS] See Cinnamic acid.
Hazard Classes and CategoriesAcute Tox. 3 (26.2%)
Safety data
- PPE
- dust mask type N95 (US), Eyeshields, Faceshields, Gloves
- wgk
- 3
- tsca
- TSCA listed
- rtecs
- GD9090000
- ridadr
- UN 2811 6.1/PG 3
- hs_code
- 2918.29.7500
- risk_code
- 22-36/37/38
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xn,Xi
- safety_code
- 26-24/25-36
- hazard_class
- 6.1
- Storage Class
- 11 - Combustible Solids
- target organs
- Respiratory system
- Hazard statements
- H302-H315-H319-H335
- Limited Quantities
- 5.0 kg (11 lbs) (solid)
- Excepted Quantities
- Max Inner Pack (30g or 30ml) and Max Outer Pack (1Kg or 1L)
- Hazard Classifications
- Acute Tox. 4 OralEye Irrit. 2Skin Irrit. 2STOT SE 3
- Precautionary statements
- P261-P264-P270-P301+P312-P302+P352-P305+P351+P338
Chemistry & industry
Uses & manufacturing
General Manufacturing Information2-Propenoic acid, 3-(2-hydroxyphenyl)-, (2E)-: ACTIVE
Applications
Usesfood and beverages
General DescriptionThis substance is a primary reference substance with assigned absolute purity (considering chromatographic purity, water, residual solvents, inorganic impurities). The exact value can be found on the certificate. Produced by PhytoLab GmbH & Co. KG
Upstream & downstream products
Downstream products
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Additional notes
DefinitionChEBI: The trans-isomer of 2-coumaric acid.
Related reactions
6 records
Compound notes
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