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583-17-5 molecular structure
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(2E)-3-(2-hydroxyphenyl)prop-2-enoic acid

ChemBase ID: 1426
Molecular Formular: C9H8O3
Molecular Mass: 164.15802
Monoisotopic Mass: 164.04734412
SMILES and InChIs

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

Cite this record

CBID:1426 http://www.chembase.cn/molecule-1426.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

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

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 4.0376344  H Acceptors
H Donor LogD (pH = 5.5) 0.35907778 
LogD (pH = 7.4) -1.3093433  Log P 1.832521 
Molar Refractivity 45.0408 cm3 Polarizability 16.809118 Å3
Polar Surface Area 57.53 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P 1.9  LOG S -2.15 
Solubility (Water) 1.15e+00 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Melting Point
~210 °C (dec.) expand Show data source
217 °C (dec.)(lit.) expand Show data source
217°C expand Show data source
217(dec.)°C expand Show data source
ca 210°C dec. expand Show data source
Storage Condition
Room Temperature (15-30°C) expand Show data source
Storage Warning
Toxic/Irritant expand Show data source
RTECS
GD9090000 expand Show data source
European Hazard Symbols
Irritant Irritant (Xi) expand Show data source
Harmful Harmful (Xn) expand Show data source
UN Number
2811 expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
German water hazard class
3 expand Show data source
Hazard Class
6.1 expand Show data source
Packing Group
3 expand Show data source
Risk Statements
22-36/37/38 expand Show data source
36/37/38 expand Show data source
Safety Statements
26 expand Show data source
26-37 expand Show data source
TSCA Listed
expand Show data source
GHS Pictograms
GHS06 expand Show data source
GHS07 expand Show data source
GHS Signal Word
Danger expand Show data source
GHS Hazard statements
H301-H315-H319-H335 expand Show data source
H315-H319-H335 expand Show data source
GHS Precautionary statements
P261-P301 + P310-P305 + P351 + P338 expand Show data source
P261-P305+P351+P338-P302+P352-P321-P405-P501A expand Show data source
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Faceshields, Gloves expand Show data source
RID/ADR
UN 2811 6.1/PG 3 expand Show data source
Purity
~97% expand Show data source
≥97.0% (HPLC) expand Show data source
97% expand Show data source
98+% expand Show data source
Grade
purum expand Show data source
Certificate of Analysis
Download expand Show data source
Download expand Show data source
Linear Formula
HOC6H4CH=CHCO2H expand Show data source
Empirical Formula (Hill Notation)
C9H8O3 expand Show data source
Classification
Genuine Natural Compounds expand Show data source

DETAILS

DETAILS

MP Biomedicals MP Biomedicals DrugBank DrugBank Apollo Scientific Apollo Scientific Wikipedia Wikipedia Sigma Aldrich Sigma Aldrich
MP Biomedicals - 05206912 external link
MP Biomedicals Rare Chemical collection
MP Biomedicals - 02150712 external link
Crystalline
Purity: ~97%
Predominantly trans-isomer.
DrugBank - DB01650 external link
Drug information: experimental
Apollo Scientific Ltd - OR40640 external link
Mixture of cis/trans isomers
Sigma Aldrich - H22809 external link
Packaging
25 g in poly bottle
5 g in glass bottle

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • 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).
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PATENTS

PATENTS

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INTERNET

INTERNET

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