Showing Compound Phytanic acid (FDB022252)

Record Information

Version

1.0

Creation date

2011-09-21 00:10:54 UTC

Update date

2019-11-26 03:21:02 UTC

Primary ID

FDB022252

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Phytanic acid

Description

A 20-carbon branched chain fatty acid, Phytanic acid is present in animal (primarily herbivores or omnivores) tissues where it may be derived from the chlorophyll in consumed plant material. Phytanic acid derives from the corresponding alcohol, phytol, and is ultimately oxidized into pristanic acid. In phytanic acid storage disease (Refsum disease) this lipid may comprise as much as 30% of the total fatty acids in plasma. These high levels in Refsum disease (a neurological disorder) are due to a phytanic acid alpha-hydroxylase deficiency.; A 20-carbon branched chain fatty acid. In phytanic acid storage disease (Refsum disease) this lipid may comprise as much as 30% of the total fatty acids of the plasma. This is due to a phytanic acid alpha-hydroxylase deficiency. [HMDB]

CAS Number

14721-66-5

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
3,7,11,15-Tetramethyl hexadecanoic acid	ChEBI
3,7,11,15-Tetramethyl-hexadecanoic acid	ChEBI
3,7,11,15-Tetramethyl-hexadecansaeure	ChEBI
3,7,11,15-Tetramethylhexadecanoic acid	Kegg
3,7,11,15-Tetramethyl hexadecanoate	Generator
3,7,11,15-Tetramethyl-hexadecanoate	Generator
3,7,11,15-Tetramethylhexadecanoate	Generator
Phytanate	Generator
3,7,11,15-Tetramethylhexadecoanoate	HMDB
3,7,11,15-Tetramethylhexadecoanoic acid	HMDB
Phytanoate	HMDB
Phytanoic acid	HMDB
Acid, phytanic	HMDB
3,7,11,15-tetramethylhexadecoanoate	hmdb
3,7,11,15-tetramethylhexadecoanoic acid	hmdb

Predicted Properties

Property	Value	Source
Water Solubility	8.2e-05 g/L	ALOGPS
logP	7.28	ALOGPS
logP	7.4	ChemAxon
logS	-6.6	ALOGPS
pKa (Strongest Acidic)	5.04	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	14	ChemAxon
Refractivity	95.28 m³·mol⁻¹	ChemAxon
Polarizability	41.09 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C20H40O2

IUPAC name

3,7,11,15-tetramethylhexadecanoic acid

InChI Identifier

InChI=1S/C20H40O2/c1-16(2)9-6-10-17(3)11-7-12-18(4)13-8-14-19(5)15-20(21)22/h16-19H,6-15H2,1-5H3,(H,21,22)

InChI Key

RLCKHJSFHOZMDR-UHFFFAOYSA-N

Isomeric SMILES

CC(C)CCCC(C)CCCC(C)CCCC(C)CC(O)=O

Average Molecular Weight

312.5304

Monoisotopic Molecular Weight

312.302830524

Classification

Description

Belongs to the class of organic compounds known as acyclic diterpenoids. These are diterpenoids (compounds made of four consecutive isoprene units) that do not contain a cycle.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Acyclic diterpenoids

Alternative Parents

Substituents

Acyclic diterpenoid
Long-chain fatty acid
Methyl-branched fatty acid
Branched fatty acid
Fatty acyl
Fatty acid
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

long-chain fatty acid (CHEBI:16285 )
branched-chain saturated fatty acid (CHEBI:16285 )
methyl-branched fatty acid (CHEBI:16285 )
Acyclic diterpenoids (C01607 )

Ontology

Ingestion

Source:

Biological:

Animal

Biological location:

Organ and components:

Cell and elements:

Extracellular

Cell:

Fibroblast

Subcellular:

Biofluid and excreta:

Process

Naturally occurring process:

Biological process:

Biochemical process:

Chemical reaction:

Lipid peroxidation

Biochemical pathway:

Lipid metabolism pathway

Cellular process:

Cell signaling

Role

Industrial application:

Red meat

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Solid
Physical Description	Not Available
Mass Composition	Not Available
Melting Point	Not Available
Boiling Point	Not Available
Experimental Water Solubility	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	Phytanic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0006-9780000000-d08f456f5acb304b7ea2	Spectrum
Predicted GC-MS	Phytanic acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00y0-9443000000-5bbc79ddca11ee15c346	Spectrum
Predicted GC-MS	Phytanic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Phytanic acid, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-03di-0009000000-1344b5ce122597753d72	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-00e9-9000000000-d058ed1cd7bf2496d801	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-01b9-9000000000-b91cf96bf3e1ed9907c9	2012-07-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0002-0192000000-404c7c552fbd445291f4	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00mk-4790000000-c4c72f2a0388e83c4d50	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9720000000-e2429e81001f3469126a	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03xr-0089000000-e67aa3a53cb223588ace	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-02tc-1094000000-c8ba97412b0185f5a5b3	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-8590000000-02e2e52e9c0e6f20a064	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-0009000000-849ba1e3311607445182	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03di-0029000000-1d86a3df25ae3d6f62b5	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-06r6-8393000000-8564c0781362b5ca2da4	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-4569000000-0ae84af33d4a6cee1563	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-06y9-9720000000-8d0e05ef1818d392c4fb	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4l-9000000000-19bc307031b7da7b3414	2021-09-25	View Spectrum