Showing Compound Monoethylhexyl phthalic acid (FDB029358)

Record Information

Version

1.0

Creation date

2011-09-21 01:54:35 UTC

Update date

2018-05-29 01:54:44 UTC

Primary ID

FDB029358

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Monoethylhexyl phthalic acid

Description

Monoethylhexyl phthalic acid (MEHP) is an active metabolite of Bis(2-ethylhexyl)phthalate (DEHP). DEHP measured from the blood of pregnant women have been significantly associated with the decreased penis width, shorter anogenital distance, and the incomplete descent of testes of their newborn sons, replicating effects identified in animals. DEHP hydrolyzes to MEHP via the enzyme Bis(2-ethylhexyl)phthalate acylhydrolase(3.1.1.60)and subsequently to phthalate salts. The released alcohol is susceptible to oxidation to the aldehyde and carboxylic acid. [HMDB]

CAS Number

4376-20-9

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

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Synonym	Source
(2-Ethylhexyl) hydrogen phthalate	ChEBI
(2-Ethylhexyl) hydrogen phthalic acid	Generator
1,2-Benzenedicarboxylate, mono(2-ethylhexyl) ester	Generator
1,2-Benzenedicarboxylic acid, mono(2-ethylhexyl) ester	ChEBI
1,2-Benzenedicarboxylicacid,mono(2-ethylhexyl)ester	HMDB
1,2-benzenedicarboxylicacid,mono(2-ethylhexyl)ester	hmdb
2-([(2-Ethylhexyl)oxy]carbonyl)benzoate	Generator
2-([(2-Ethylhexyl)oxy]carbonyl)benzoic acid	ChEBI
2-Ethylhexyl hydrogen phthalate	ChEBI
2-ETHYLHEXYL HYDROGEN PHTHALATE	hmdb

Showing 1 to 10 of 57 entries

Predicted Properties

Property	Value	Source
Water Solubility	0.013 g/L	ALOGPS
logP	4.36	ALOGPS
logP	4.66	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Acidic)	3.08	ChemAxon
pKa (Strongest Basic)	-7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	63.6 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	77.49 m³·mol⁻¹	ChemAxon
Polarizability	30.96 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C16H22O4

IUPAC name

2-{[(2-ethylhexyl)oxy]carbonyl}benzoic acid

InChI Identifier

InChI=1S/C16H22O4/c1-3-5-8-12(4-2)11-20-16(19)14-10-7-6-9-13(14)15(17)18/h6-7,9-10,12H,3-5,8,11H2,1-2H3,(H,17,18)

InChI Key

DJDSLBVSSOQSLW-UHFFFAOYSA-N

Isomeric SMILES

CCCCC(CC)COC(=O)C1=CC=CC=C1C(O)=O

Average Molecular Weight

278.3435

Monoisotopic Molecular Weight

278.151809192

Classification

Description

Belongs to the class of organic compounds known as benzoic acid esters. These are ester derivatives of benzoic acid.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

Benzoic acid esters

Alternative Parents

Substituents

Benzoate ester
Benzoic acid
Benzoyl
Dicarboxylic acid or derivatives
Carboxylic acid ester
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

dicarboxylic acid monoester (CHEBI:17243 )
phthalate ester (CHEBI:17243 )

Ontology

Disposition

Source:

Endogenous

Biological location:

Subcellular:

Biofluid and excreta:

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

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Property	Value	Reference
Boiling Point	Not Available
Charge	Not Available
Density	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Experimental Water Solubility	Not Available
Isoelectric point	Not Available
Mass Composition	Not Available
Melting Point	Not Available
Optical Rotation	Not Available

Showing 1 to 10 of 14 entries

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
EI-MS	Mass Spectrum (Electron Ionization)	splash10-0002-4900000000-af0f2c76a7c01b845a00	2014-09-20	View Spectrum
GC-MS	Monoethylhexyl phthalic acid, non-derivatized, GC-MS Spectrum	splash10-00dj-2970000000-346112e2dd7eb2ef672f	Spectrum
GC-MS	Monoethylhexyl phthalic acid, non-derivatized, GC-MS Spectrum	splash10-00dj-2970000000-346112e2dd7eb2ef672f	Spectrum
Predicted GC-MS	Monoethylhexyl phthalic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0002-5920000000-6756fbba86aadca647ce	Spectrum
Predicted GC-MS	Monoethylhexyl phthalic acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00di-7392000000-fd40ccd8c52320562e5c	Spectrum
Predicted GC-MS	Monoethylhexyl phthalic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-006t-0960000000-efbb62fb904150b613f2	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 15V, Positive	splash10-006t-0960000000-bace63e54682391af671	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 45V, Positive	splash10-00kb-0910000000-77eed661ab413010d354	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 60V, Positive	splash10-00mk-0900000000-214bdb75cf5614522a03	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 45V, Negative	splash10-00ai-0900000000-d636e4277afd375744d2	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 30V, Negative	splash10-001i-0900000000-e6f221aefc0e24f648d5	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 75V, Positive	splash10-002b-0900000000-d8cdf715271ec6e661b8	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 15V, Negative	splash10-0059-0940000000-bbc0013de532edede483	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 90V, Negative	splash10-004i-9100000000-d5a5ecd4f3c706f53a0f	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 45V, Positive	splash10-00kb-0910000000-a2eba6e125597cb7530d	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 60V, Negative	splash10-00b9-2900000000-1d8439ed7614ed714822	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 75V, Negative	splash10-004i-9800000000-3f611dc53f826ce06536	2021-09-20	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03fr-0790000000-972234c38f1e6baf9909	2016-08-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03di-4930000000-1ab987bce4973d4f07f4	2016-08-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4l-9500000000-53028683cce560c7a65b	2016-08-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0490000000-44a004dad8099c4e00de	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00w9-1940000000-8169435369a241584a63	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00fr-6900000000-56a7cc157be52d6494f3	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-0290000000-bf11acdb8d5f1fa06aa5	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0532-2940000000-474dfefcab564610df5f	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9500000000-0b315e8ad86892867d12	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0290000000-048ea11376b7fe328007	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00b9-5950000000-012e94386a547e3c0c23	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9410000000-a8dbecb62f34e602da89	2021-09-25	View Spectrum

NMR

Type	Description		View

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

17243

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB13248

CRC / DFC (Dictionary of Food Compounds) ID

Not Available

EAFUS ID

Not Available

Dr. Duke ID

Not Available

BIGG ID

Not Available

KNApSAcK ID

Not Available

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Not Available

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

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Food	Content Range	Average	Reference

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Biological Effects and Interactions

Health Effects / Bioactivities

Not Available

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Not Available

Files

MSDS

Not Available

References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference

Showing Compound Monoethylhexyl phthalic acid (FDB029358)

Structure for FDB029358 (Monoethylhexyl phthalic acid)