Showing Compound Sebacic acid (FDB022247)

Record Information

Version

1.0

Creation date

2011-09-21 00:10:50 UTC

Update date

2019-11-26 03:21:01 UTC

Primary ID

FDB022247

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Sebacic acid

Description

Sebacic acid is a saturated, straight-chain naturally occurring dicarboxylic acid with 10 carbon atoms. Sebacic acid is a normal urinary acid. In patients with multiple acyl-CoA-dehydrogenase deficiency (MADD) or glutaric aciduria type II (GAII) are a group of metabolic disorders due to deficiency of either electron transfer flavoprotein or electron transfer flavoprotein ubiquinone oxidoreductase, biochemical data shows an increase in urine sebacic acid excretion. Sebacic acid is a white flake or powdered crystal slightly soluble in water that has been proposed as an alternative energy substrate in total parenteral nutrition. Sebacic Acid was named from the Latin sebaceus (tallow candle) or sebum (tallow) in reference to its use in the manufacture of candles. Sebacic Acid and its derivatives such as azelaic acid have a variety of industrial uses as plasticizers, lubricants, hydraulic fluids, cosmetics, candles, etc. It is used in the synthesis of polyamide and alkyd resins. It is also used as an intermediate for aromatics, antiseptics and painting materials. (PMID: 10556649, 1738216, 8442769, 12706375) [HMDB]

CAS Number

111-20-6

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
1,10-Decanedioic acid	ChEBI
1,8-Dicarboxyoctane	ChEBI
Decanedioic acid	ChEBI
Sebacinsaeure	ChEBI
1,10-Decanedioate	Generator
Decanedioate	Generator
Sebacate	Generator
1,8-Octanedicarboxylate	HMDB
1,8-Octanedicarboxylic acid	HMDB
4,7-Dioxosebacic acid	HMDB
4-Oxodecanedioate	HMDB
4-Oxodecanedioic acid	HMDB
Acide sebacique	HMDB
Decanedicarboxylic acid	HMDB
Dicarboxylic acid C10	HMDB
Ipomic acid	HMDB
N-Decanedioate	HMDB
N-Decanedioic acid	HMDB
Sebacic acids	HMDB
Sebacinsaure	HMDB
Seracic acid	HMDB
Sebacic acid, aluminum salt	HMDB
Sebacic acid, monocadmium salt	HMDB
Sebacic acid, sodium salt	HMDB
4-oxodecanedioate	hmdb
4-oxodecanedioic acid	hmdb
4,7-dioxosebacic acid	hmdb
acide sebacique	hmdb
n-Decanedioate	hmdb
n-Decanedioic acid	hmdb
sebacic acid	hmdb

Predicted Properties

Property	Value	Source
Water Solubility	0.91 g/L	ALOGPS
logP	1.93	ALOGPS
logP	2.27	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	4.72	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	74.6 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	51.14 m³·mol⁻¹	ChemAxon
Polarizability	22.61 Å³	ChemAxon
Number of Rings	0	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

C10H18O4

IUPAC name

decanedioic acid

InChI Identifier

InChI=1S/C10H18O4/c11-9(12)7-5-3-1-2-4-6-8-10(13)14/h1-8H2,(H,11,12)(H,13,14)

InChI Key

CXMXRPHRNRROMY-UHFFFAOYSA-N

Isomeric SMILES

OC(=O)CCCCCCCCC(O)=O

Average Molecular Weight

202.2475

Monoisotopic Molecular Weight

202.120509064

Classification

Description

Belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Medium-chain fatty acids

Alternative Parents

Substituents

Medium-chain fatty acid
Dicarboxylic 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

alpha,omega-dicarboxylic acid (CHEBI:41865 )
Dicarboxylic acids (C08277 )
Dicarboxylic acids (LMFA01170006 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Synthetic:

Personal care product

Biological location:

Subcellular:

Biofluid and excreta:

Process

Naturally occurring process:

Biological process:

Biochemical process:

Biochemical pathway:

Lipid metabolism pathway

Chemical reaction:

Lipid peroxidation

Role

Biological role:

Industrial application:

Personal care products

Pharmaceutical industry:

Pharmaceutical

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
EI-MS	Mass Spectrum (Electron Ionization)	splash10-0532-9200000000-34e843efdffcce316afd	2014-09-20	View Spectrum
GC-MS	Sebacic acid, 2 TMS, GC-MS Spectrum	splash10-00mk-2910000000-944d83241331f8be19a6	Spectrum
GC-MS	Sebacic acid, non-derivatized, GC-MS Spectrum	splash10-00mk-1910000000-2e3fc1189a96874a25c9	Spectrum
GC-MS	Sebacic acid, 2 TMS, GC-MS Spectrum	splash10-00fr-9400000000-d288a779699c505fde08	Spectrum
GC-MS	Sebacic acid, 2 TMS, GC-MS Spectrum	splash10-00pj-3910000000-87feed2c593dbff7fae8	Spectrum
GC-MS	Sebacic acid, non-derivatized, GC-MS Spectrum	splash10-00mk-2910000000-944d83241331f8be19a6	Spectrum
GC-MS	Sebacic acid, non-derivatized, GC-MS Spectrum	splash10-00mk-1910000000-2e3fc1189a96874a25c9	Spectrum
GC-MS	Sebacic acid, non-derivatized, GC-MS Spectrum	splash10-00fr-9400000000-d288a779699c505fde08	Spectrum
GC-MS	Sebacic acid, non-derivatized, GC-MS Spectrum	splash10-00pj-3910000000-87feed2c593dbff7fae8	Spectrum
Predicted GC-MS	Sebacic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0006-9600000000-0d93a938bd873800d5e0	Spectrum
Predicted GC-MS	Sebacic acid, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00g0-9750000000-c51f62deffa53727f438	Spectrum
Predicted GC-MS	Sebacic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Sebacic acid, TMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Sebacic acid, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Sebacic acid, TBDMS_2_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, Negative (Annotated)	splash10-0udi-0290000000-cd204cf662cb75a52f8c	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)	splash10-0540-5910000000-d9df3022a95972158b37	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)	splash10-0ue9-9660000000-49a78126c0d15f6e3eb7	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-0udi-0090000000-841b953970b4cd52f8be	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-0uei-0950000000-001fe11fe26a2d644897	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-000i-0900000000-83a69e4c3ab60df51781	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-08i9-7900000000-951787b9bed084d77a6b	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-057i-9000000000-83b9d67dcdf5f385ab57	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-0f80-0950000000-7fec916790f882e8630a	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0udi-0090000000-841b953970b4cd52f8be	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0uei-0950000000-001fe11fe26a2d644897	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-000i-0900000000-83a69e4c3ab60df51781	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-08i9-7900000000-951787b9bed084d77a6b	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-057i-9000000000-83b9d67dcdf5f385ab57	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-IT , negative	splash10-0019-0900000000-e9711749ce4f183c8c63	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-0f80-0950000000-e264d8b786405e562fd4	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - , positive	splash10-007d-8900000000-fb7880caeb9e996f8bba	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - 15V, Negative	splash10-0uei-0960000000-b0edb62684a8bf743208	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 30V, Negative	splash10-0f80-0930000000-e6d1038fa517b1259227	2021-09-20	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udr-0970000000-b21ac000bbddcd19753b	2017-07-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0k9l-2910000000-aad49769e8652ff2ea40	2017-07-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-06rw-9200000000-bab98f63e58992b52316	2017-07-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0290000000-f600fa6f22d1c40d97d5	2017-07-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0zfr-2790000000-3f24f2c725d420658a66	2017-07-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9300000000-1aa6408615ab7e415691	2017-07-26	View Spectrum

NMR

Type	Description		View
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)		Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CD₃OD, experimental)		Spectrum