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(E)-para-hydroxycinnamic acid
2-propenoic acid, 3-(4-hydroxyphenyl)-, (E)- (9CI)

Supplier Sponsors

Name:(E)-3-(4-hydroxyphenyl)prop-2-enoic acid
CAS Number: 501-98-4Picture of molecule3D/inchi
FDA UNII:IBS9D1EU3J
Nikkaji Web:J6.196D
Beilstein Number:2207381
MDL:MFCD00004399
XlogP3:1.50 (est)
Molecular Weight:164.16036000
Formula:C9 H8 O3
BioActivity Summary:listing
NMR Predictor:Predict (works with chrome or firefox)
Category:natural substances and extractives
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Google Scholar:Search
Google Books:Search
Google Scholar: with word "volatile"Search
Google Scholar: with word "flavor"Search
Google Scholar: with word "odor"Search
Google Patents:Search
US Patents:Search
EU Patents:Search
Pubchem Patents:Search
PubMed:Search
NCBI:Search
 
Physical Properties:
Assay: 95.00 to 100.00
Food Chemicals Codex Listed: No
Melting Point: 214.00 °C. @ 760.00 mm Hg
Boiling Point: 346.00 to 347.00 °C. @ 760.00 mm Hg (est)
Flash Point: 351.00 °F. TCC ( 177.30 °C. ) (est)
logP (o/w): 1.460
Soluble in:
 alcohol
 water, 1.83e+004 mg/L @ 25 °C (est)
 
Organoleptic Properties:
Odor Strength:medium
Odor Description:at 100.00 %. balsamic
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
None found
 
Suppliers:
BOC Sciences
For experimental / research use only.
trans-4-Hydroxycinnamic acid 0.98
Odor: characteristic
Use: trans-4-Hydroxycinnamic acid isolated from the herb of Trifolium pratense. It has anti-bacteria effect against some gram-positive and gram-negative bacteria. antibacterial; antimicrobial;
Glentham Life Sciences
4-Hydroxycinnamic acid
Penta International
TRANS-P-HYDROXYCINNAMIC ACID
Santa Cruz Biotechnology
For experimental / research use only.
p-Coumaric acid ≥99%
Sigma-Aldrich: Sigma
For experimental / research use only.
p-Coumaric acid ≥98.0% (HPLC)
TCI AMERICA
For experimental / research use only.
trans-p-Coumaric Acid >98.0%(GC)(T)
 
Safety Information:
Preferred SDS: View
 
Hazards identification
 
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
 
Pictogram
 
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
oral-mouse LD50 2850 mg/kg
BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION
Gendai no Rinsho. Vol. 3, Pg. 675, 1969.

intraperitoneal-mouse LD50 1160 mg/kg
BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION
Gendai no Rinsho. Vol. 3, Pg. 675, 1969.

Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
 
Safety in Use Information:
Category:
natural substances and extractives
Recommendation for (E)-para-hydroxycinnamic acid usage levels up to:
 not for fragrance use.
 
Recommendation for (E)-para-hydroxycinnamic acid flavor usage levels up to:
 not for flavor use.
 
Safety References:
EPI System: View
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :637542
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:2
(E)-3-(4-hydroxyphenyl)prop-2-enoic acid
Chemidplus:0000501984
RTECS:GD9095000 for cas# 501-98-4
 
References:
 (E)-3-(4-hydroxyphenyl)prop-2-enoic acid
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):637542
Pubchem (sid):134978583
Flavornet:501-98-4
 
Other Information:
(IUPAC):Atomic Weights of the Elements 2011 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
CHEBI:View
CHEMBL:View
Golm Metabolome Database:Search
KEGG (GenomeNet):C00811
HMDB (The Human Metabolome Database):HMDB02035
FooDB:FDB002594
YMDB (Yeast Metabolome Database):YMDB00498
Export Tariff Code:2918.29.2000
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
 
Potential Blenders and core components note
None Found
 
Potential Uses:
None Found
 
Occurrence (nature, food, other):note
 alfalfa
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 apple plant
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 artichoke jerusalem artichoke
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 cherry black cherry
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 clover red clover
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 coffee
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 coriander fruit
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 coriander plant
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 coriander seed
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 cynomorium songaricum
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 orange fruit juice
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 pea
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 sage
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 wasabi
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Synonyms:
 cinnamic acid, p-hydroxy-, (E)-
(E)-p-coumaric acid
(E)-para-coumaric acid
trans-4-coumaric acid
trans-p-coumaric acid
trans-para-coumaric acid
(E)-p-coumarinic acid
(E)-para-coumarinic acid
trans-p-coumarinic acid
trans-para-coumarinic acid
(E)-3-(4-hydroxy-phenyl)-acrylic acid
(E)-4-hydroxycinnamic acid
(E)-p-hydroxycinnamic acid
trans-4-hydroxycinnamic acid
trans-p-hydroxycinnamic acid
trans-para-hydroxycinnamic acid
4-hydroxycinnamic acid (predominantly trans)
(E)-3-(4-hydroxyphenyl)-2-propenoic acid
(2E)-3-(4-hydroxyphenyl)acrylic acid
(2E)-3-(4-hydroxyphenyl)acrylsäure
(2E)-3-(4-hydroxyphenyl)prop-2-enoic acid
(E)-3-(4-hydroxyphenyl)prop-2-enoic acid
(E)-naringeninic acid
2-propenoic acid, 3-(4-hydroxyphenyl)-, (2E)-
2-propenoic acid, 3-(4-hydroxyphenyl)-, (E)- (9CI)
 

Articles:

PubMed:Granatumins A-G, limonoids from the seeds of a Krishna mangrove, Xylocarpus granatum.
PubMed:Toxicity of cassia and cinnamon oil compounds and cinnamaldehyde-related compounds to Sitophilus oryzae (Coleoptera: Curculionidae).
PubMed:Induction of 4-hydroxycinnamate decarboxylase in Klebsiella oxytoca cells exposed to substrates and non-substrate 4-hydroxycinnamate analogs.
PubMed:Stereochemically specific proton transfer in decarboxylation of 4-hydroxycinnamic acids by 4-hydroxycinnamate decarboxylase from Klebsiella oxytoca.
PubMed:Trans/cis (Z/E) photoisomerization of the chromophore of photoactive yellow protein is not a prerequisite for the initiation of the photocycle of this photoreceptor protein.
 
Notes:
isolated from cynomorium songaricum Widespread in plants, e.g. peel of black cherry (Prunus serotina), lentil seeds and from red clover (Trifolium pratense). Found by Bate-Smith in 48% of investigated dicotyledonous and 55% of monocotyledonous spp. Coumaric acid is a hydroxycinnamic acid, an organic compound that is a hydroxy derivative of cinnamic acid. There are three isomers, o-coumaric acid, m-coumaric acid, and p-coumaric acid, that differ by the position of the hydroxy substitution of the phenyl group. p-Coumaric acid is the most abundant isomer of the three in nature. (Wikipedia)
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