ContaminantDB: 2-Ethylhexyl trans-4-methoxycinnamate

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-05-22 06:06:39 UTC

Update Date

2016-11-09 01:15:59 UTC

Accession Number

CHEM019422

Identification

Common Name

2-Ethylhexyl trans-4-methoxycinnamate

Class

Small Molecule

Description

Octinoxate is a cinnamate ester and common ingredient in sunscreen and other skin care products to minimize DNA photodamage. It was originally developed in 1950's as an organic UV-B filter that absorbs UV-B rays from sun. It is often combined with nanoparticles or other water-resistant liposomes in formulations to increase the localization at the epidermis and decrease the risk of percutaneous absorption. Its use in pharmaceutical and cosmetic formulations is approved by FDA.

Contaminant Sources

ToxCast & Tox21 Chemicals

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Octyl methoxycinnamate	Kegg
Parsol	Kegg
Octyl methoxycinnamic acid	Generator
Octyl 4-methoxycinnamate	Generator
OCTINOXic acid	HMDB
Heliopan new	HMDB
OMC cinnamate	HMDB
Parsol MCX	HMDB
Octylmethoxycinnamate	HMDB
2-Ethylhexyl-4-methoxycinnamate	HMDB
2-Ethylhexyl-p-methoxycinnamate	HMDB
Escalol 557	HMDB
Octyl-methoxycinnamate	HMDB

Chemical Formula

C₁₈H₂₆O₃

Average Molecular Mass

290.397 g/mol

Monoisotopic Mass

290.188 g/mol

CAS Registry Number

83834-59-7

IUPAC Name

2-ethylhexyl (2E)-3-(4-methoxyphenyl)prop-2-enoate

Traditional Name

parsol

SMILES

[H]\C(=C(\[H])C1=CC=C(OC)C=C1)C(=O)OCC(CC)CCCC

InChI Identifier

InChI=1S/C18H26O3/c1-4-6-7-15(5-2)14-21-18(19)13-10-16-8-11-17(20-3)12-9-16/h8-13,15H,4-7,14H2,1-3H3/b13-10+

InChI Key

YBGZDTIWKVFICR-JLHYYAGUSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as cinnamic acid esters. These are compound containing an ester derivative of cinnamic acid.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Cinnamic acids and derivatives

Sub Class

Cinnamic acid esters

Direct Parent

Cinnamic acid esters

Alternative Parents

Substituents

Cinnamic acid ester
Phenoxy compound
Anisole
Methoxybenzene
Phenol ether
Styrene
Alkyl aryl ether
Fatty acid ester
Monocyclic benzene moiety
Fatty acyl
Benzenoid
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Monocarboxylic acid or derivatives
Ether
Carboxylic acid derivative
Organic oxide
Organooxygen compound
Hydrocarbon derivative
Carbonyl group
Organic oxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.00045 g/L	ALOGPS
logP	5.62	ALOGPS
logP	5.38	ChemAxon
logS	-5.8	ALOGPS
pKa (Strongest Basic)	-4.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	35.53 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	86.44 m³·mol⁻¹	ChemAxon
Polarizability	34.84 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-06vi-9530000000-dfb5bc7b1b0717378513	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 50V, Positive	splash10-001i-0900000000-d4a1e41c086413d0cf67	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 50V, Positive	splash10-001i-0900000000-47b5b9c89e092811dc9d	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-03di-0900000000-f61c750cc4eee5641214	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-03di-0900000000-bef6ca3443465e6c192e	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-03e9-0900000000-9b48952b6721ccf2a0d4	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-004i-0900000000-04c530c6956b0f1f054f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03dl-0950000000-7c75a171098f061df1d5	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03di-3910000000-999432b0b3a154dc16c4	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-06r6-9400000000-f0de61dd27ceae8cac50	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-052r-0970000000-9b1d54a8c418b0e3d7dd	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-06vi-0910000000-29fe696309912eb4ba3d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-01r2-3900000000-58e02602b0c98e57a09c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-01r6-4970000000-a670cd89d51c4faa0f4b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-08ir-5910000000-378dcd5411abe5d4d831	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-053u-9200000000-9025b50b69c626ee01d2	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0790000000-dffcbb803f602e4748f9	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4r-0920000000-f1683c652bffc0f2fcad	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-014i-0900000000-17d9a346b3a4b2ac552f	Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Not Available

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

Not Available

Uses/Sources

Not Available

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

DB09496

HMDB ID

HMDB0061861

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Not Available

Chemspider ID

Not Available

ChEBI ID

Not Available

PubChem Compound ID

5355130

Kegg Compound ID

Not Available

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

1. Lee GS, Widjaja A, Ju YH: Enzymatic synthesis of cinnamic acid derivatives. Biotechnol Lett. 2006 Apr;28(8):581-5.

2-Ethylhexyl trans-4-methoxycinnamate (CHEM019422)

Structure for CHEM019422: 2-Ethylhexyl trans-4-methoxycinnamate