4-METHOXYCINNAMIC ACID

Details

Stereochemistry	ACHIRAL
Molecular Formula	C10H10O3
Molecular Weight	178.1846
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

COC1=CC=C(\C=C\C(O)=O)C=C1

InChI

InChIKey=AFDXODALSZRGIH-QPJJXVBHSA-N

InChI=1S/C10H10O3/c1-13-9-5-2-8(3-6-9)4-7-10(11)12/h2-7H,1H3,(H,11,12)/b7-4+

HIDE SMILES / InChI

Molecular Formula	C10H10O3
Molecular Weight	178.1846
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	1
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/25429559 | https://www.iarc.fr/en/publications/pdfs-online/prev/handbook5/Handbook5_Sunscreens-2.pdfhttps://www.ncbi.nlm.nih.gov/pubmed/15575598

Cis-4-methoxycinnamic acid is a less frequent isomer of 4-methoxycinnamic acid, isolated from from Aquilegia vulgaris.

Approval Year

Conditions

Condition	Modality	Highest Phase	Product
Unknown 2578
Bacterial infections 234 Sources: http://scialert.net/qredirect.php?doi=jbs.2006.135.139&linkid=pdf	Curative	Basic research	Unknown Approved Use Unknown
Sunburn 84 Sources: https://www.accessdata.fda.gov/scripts/cdrh/cfdocs/cfcfr/CFRSearch.cfm?fr=352.50	Preventing	Approved 8429	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
		14041847
Anti-amnestic activity of E-p-methoxycinnamic acid from Scrophularia buergeriana.	2003 Jul	12880915
E- and Z-p-methoxycinnamic acid from Aquilegia vulgaris.	2004 Jul-Aug	15575598
Esters, amides and substituted derivatives of cinnamic acid: synthesis, antimicrobial activity and QSAR investigations.	2004 Oct	15464616
The modulatory influence of p-methoxycinnamic acid, an active rice bran phenolic acid, against 1,2-dimethylhydrazine-induced lipid peroxidation, antioxidant status and aberrant crypt foci in rat colon carcinogenesis.	2012 Mar 5	22326950

Patents

Sample Use Guides

In Vivo Use Guide

Apply liberally/generously (and evenly) 15 minutes before sun exposure. Reapply at least every 2 hours.

Route of Administration: Topical

In Vitro Use Guide

Minimum inhibitory concentrations of 4-methoxycinnamic acid against M. luteus, S. aureus, E. coli and S. enteritidis were 80, 60, 50 and 60 ug mL-1, respectively.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 18:58:24 GMT 2023` Edited by `admin` on `Fri Dec 15 18:58:24 GMT 2023`
Record UNII	6G4ML8401A
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

4-METHOXYCINNAMIC ACID

Systematic Name

English

NSC-5303

Code

English

NSC-623437

Code

English

BERNEL HYDRO

Common Name

English

2-PROPENOIC ACID, 3-(4-METHOXYPHENYL)-

Systematic Name

English

(E)-4-METHOXYCINNAMIC ACID

Systematic Name

English

(E)-P-METHOXYCINNAMIC ACID

Common Name

English

TRANS-3-(4-METHOXYPHENYL)-2-PROPENOIC ACID

Systematic Name

English

Code System Code Type Description

MESH

C063318