Showing Compound Hexanedioic acid (FDB008309)

Record Information

Version

1.0

Creation date

2010-04-08 22:08:01 UTC

Update date

2019-11-26 03:02:26 UTC

Primary ID

FDB008309

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Hexanedioic acid

Description

Constituent of beet juice, pork fat, guava fruit (Psidium guajava), papaya (Carica papaya) and raspberry (Rubus idaeus). Food acidulant Adipic acid is a compound of the class of carboxylic acids that is derived from oxidation of various fats. It is a white crystalline powder appearing as an acid in aqueous circumstances, though it is not highly soluble (wikipedia); Adipic acid, like most carboxylic acids, is a mild skin irritant. It is mildly toxic, with LD50 of 3600 mg/kg for oral ingestion by rats.; By far the majority of the 2.5 billion kg of adipic acid produced annually is used as monomer for the production of nylon by a polycondensation reaction with hexamethylene diamine forming 6,6-nylon. Other major applications also involve polymers: it is a monomer for production of Polyurethane and its esters are plasticizers, especially in PVC. Hexanedioic acid is found in many foods, some of which are common beet, red beetroot, fats and oils, and root vegetables.

CAS Number

124-04-9

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
1,4-Butanedicarboxylic acid	ChEBI
1,6-Hexanedioic acid	ChEBI
Adipinic acid	ChEBI
Adipinsaeure	ChEBI
e 355	ChEBI
e-355	ChEBI
e355	ChEBI
INS no. 355	ChEBI
Hexanedioate	Kegg
Hexan-1,6-dicarboxylate	Kegg
1,4-Butanedicarboxylate	Generator
1,6-Hexanedioate	Generator
Adipinate	Generator
Hexanedioic acid	Generator
Hexan-1,6-dicarboxylic acid	Generator
Adipate	Generator
Acifloctin	HMDB
Acinetten	HMDB
Adi-pure	HMDB
Adilactetten	HMDB
Kyselina adipova	HMDB
Molten adipate	HMDB
Molten adipic acid	HMDB
Adipic acid, calcium salt	HMDB
Adipic acid, disodium salt	HMDB
Sodium adipate	HMDB
Adipic acid, cu(+2) salt	HMDB
Adipic acid, cu(+2) salt (1:1)	HMDB
Adipic acid, diammonium salt	HMDB
Adipic acid, sodium salt	HMDB
Adipic acid, cu salt	HMDB
Adipic acid, potassium salt	HMDB
Ammonium adipate	HMDB
Magnesium adipate	HMDB
Adipic acid, MG salt (1:1)	HMDB
Adipic acid, monoammonium salt	HMDB
Adipic acid, nickel salt	HMDB
Diammonium adipate	HMDB
Adipic acid	KEGG
1, 4-Butanedicarboxylic acid	biospider
1,6-HEXANE-DIOIC ACID	biospider
3385-41-9 (di-ammonium salt)	biospider
7486-38-6 (di-hydrochloride salt)	biospider
7486-39-7 (magnesium[1:1] salt)	biospider
Adi-pure high purity adipic acid	biospider
Adi-pure lga adipic acid	biospider
Adi-pure(r) high purity adipic acid	biospider
Adi-pure(r) lga adipic acid	biospider
Butane-1,4-dicarboxylic acid	db_source
E355	db_source
FEMA 2011	db_source
Hexanedioc acid	biospider
Hexanedioic acid, sodium salt	biospider

Predicted Properties

Property	Value	Source
Water Solubility	32.2 g/L	ALOGPS
logP	0.13	ALOGPS
logP	0.49	ChemAxon
logS	-0.66	ALOGPS
pKa (Strongest Acidic)	3.92	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	5	ChemAxon
Refractivity	32.74 m³·mol⁻¹	ChemAxon
Polarizability	14.24 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C6H10O4

IUPAC name

hexanedioic acid

InChI Identifier

InChI=1S/C6H10O4/c7-5(8)3-1-2-4-6(9)10/h1-4H2,(H,7,8)(H,9,10)

InChI Key

WNLRTRBMVRJNCN-UHFFFAOYSA-N

Isomeric SMILES

OC(=O)CCCCC(O)=O

Average Molecular Weight

146.1412

Monoisotopic Molecular Weight

146.057908808

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:30832 )
Dicarboxylic acids (LMFA01170048 )

Ontology

Physiological effect

Health effect:

Health condition:

Anorexia nervosa

Metabolism and nutrition disorders:

Glutaric aciduria type 2

Cancer:

Lung cancer

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Synthetic:

Personal care product

Biological:

Plant

Microbe:

Escherichia:

Escherichia coli

Biological location:

Organ and components:

Biofluid and excreta:

Subcellular:

Process

Naturally occurring process:

Biological process:

Biochemical process:

Biochemical pathway:

Lipid metabolism pathway

Chemical reaction:

Lipid peroxidation

Role

Environmental role:

Air pollutant

Industrial application:

Biological role:

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Liquid
Physical Description	Not Available
Mass Composition	C 49.31%; H 6.90%; O 43.79%	DFC
Melting Point	Mp 153° (149-150°)	DFC
Boiling Point	Bp15 216°	DFC
Experimental Water Solubility	30.8 mg/mL at 34 oC	YALKOWSKY,SH & DANNENFELSER,RM (1992)
Experimental logP	0.08	HANSCH,C ET AL. (1995)
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)	splash10-0f6x-9200000000-988f76bb42297a8d9d3b	Spectrum
GC-MS	Hexanedioic acid, non-derivatized, GC-MS Spectrum	splash10-03dj-0900000000-5378ec232b7bc8c84368	Spectrum
GC-MS	Hexanedioic acid, 2 TMS, GC-MS Spectrum	splash10-03di-2920000000-a4bb0f67851a49bcd19c	Spectrum
GC-MS	Hexanedioic acid, non-derivatized, GC-MS Spectrum	splash10-0a6u-9000000000-36d8bc2f7d1a77a7b466	Spectrum
GC-MS	Hexanedioic acid, non-derivatized, GC-MS Spectrum	splash10-03dm-0910000000-596aa8217b629d682b81	Spectrum
GC-MS	Hexanedioic acid, non-derivatized, GC-MS Spectrum	splash10-03dj-0900000000-5378ec232b7bc8c84368	Spectrum
GC-MS	Hexanedioic acid, non-derivatized, GC-MS Spectrum	splash10-03di-2920000000-a4bb0f67851a49bcd19c	Spectrum
GC-MS	Hexanedioic acid, non-derivatized, GC-MS Spectrum	splash10-03dj-0900000000-60ba84e1d479d88e3fac	Spectrum
Predicted GC-MS	Hexanedioic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0fk9-9300000000-c0da1d9e52f67b1d7dbc	Spectrum
Predicted GC-MS	Hexanedioic acid, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00dr-9620000000-9525dd4ed0f987b19a68	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)	splash10-000x-3900000000-1c5a6a5287f8fd7736f1	Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)	splash10-001i-9100000000-3e9496a6da881edd91e0	Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)	splash10-0uea-9500000000-edb5529010e4b88414c4	Spectrum
MS/MS	LC-MS/MS Spectrum - EI-B (Unknown) , Positive	splash10-0a6u-9000000000-36d8bc2f7d1a77a7b466	Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-0002-0900000000-a1852cfc66b4feae9b18	Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-0ue9-6900000000-90e783cc3522f0ce7880	Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-001i-9200000000-b5a64d560d8bc62d8d51	Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-001i-9000000000-a96d5ee9551b944e4db8	Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-001i-9000000000-2e61b7d2a4dbc9867123	Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0002-0900000000-a1852cfc66b4feae9b18	Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0ue9-6900000000-90e783cc3522f0ce7880	Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-001i-9200000000-b5a64d560d8bc62d8d51	Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-001i-9000000000-a96d5ee9551b944e4db8	Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-001i-9000000000-2e61b7d2a4dbc9867123	Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-0002-2900000000-983aa19fb3183a9bc5ab	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004j-0900000000-ece39ae1f752cf2970f1	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0fba-5900000000-682fc79230e6f03bacfb	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-052f-9000000000-66b61bf2c65c15bb7fed	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0900000000-ec5d2c95f1dac5349608	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-002b-2900000000-27613c7de7a721350bb8	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-9100000000-78804e4122c63b62ca5b	Spectrum

NMR

Type	Description	View
1D NMR	13C NMR Spectrum	Spectrum
1D NMR	1H NMR Spectrum	Spectrum
1D NMR	1H NMR Spectrum	Spectrum
1D NMR	13C NMR Spectrum	Spectrum
2D NMR	[1H,13C] 2D NMR Spectrum	Spectrum

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

30832

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB00448

CRC / DFC (Dictionary of Food Compounds) ID

DFV47-H:DFV47-H

EAFUS ID

Dr. Duke ID

ADIPIC-ACID

BIGG ID

Not Available

KNApSAcK ID

C00001178

HET ID

0L1

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

rw1001801

SuperScent ID

Not Available

Wikipedia ID

Adipic acid

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Descriptor	ID	Definition	Reference
acidulant	64047	Any substance which is added to food to preserve or enhance its flavour and/or appearance.	DUKE
irritant			DUKE
perfumery	48318	A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell.	DUKE

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Flavor	Citations
odorless	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.

Files

MSDS

show

References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference

— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.
— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).