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Hexanedioic acid (FDB008309)

Record Information
Version1.0
Creation date2010-04-08 22:08:01 UTC
Update date2019-11-26 03:02:26 UTC
Primary IDFDB008309
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameHexanedioic acid
DescriptionConstituent 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 Number124-04-9
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
Not AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility32.2 g/LALOGPS
logP0.13ALOGPS
logP0.49ChemAxon
logS-0.66ALOGPS
pKa (Strongest Acidic)3.92ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area74.6 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity32.74 m³·mol⁻¹ChemAxon
Polarizability14.24 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC6H10O4
IUPAC namehexanedioic acid
InChI IdentifierInChI=1S/C6H10O4/c7-5(8)3-1-2-4-6(9)10/h1-4H2,(H,7,8)(H,9,10)
InChI KeyWNLRTRBMVRJNCN-UHFFFAOYSA-N
Isomeric SMILESOC(=O)CCCCC(O)=O
Average Molecular Weight146.1412
Monoisotopic Molecular Weight146.057908808
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.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentMedium-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 FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Environmental role:

Industrial application:

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateLiquid
Physical DescriptionNot Available
Mass CompositionC 49.31%; H 6.90%; O 43.79%DFC
Melting PointMp 153° (149-150°)DFC
Boiling PointBp15 216°DFC
Experimental Water Solubility30.8 mg/mL at 34 oCYALKOWSKY,SH & DANNENFELSER,RM (1992)
Experimental logP0.08HANSCH,C ET AL. (1995)
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-0f6x-9200000000-988f76bb42297a8d9d3b2014-09-20View Spectrum
GC-MSHexanedioic acid, non-derivatized, GC-MS Spectrumsplash10-03dj-0900000000-5378ec232b7bc8c84368Spectrum
GC-MSHexanedioic acid, 2 TMS, GC-MS Spectrumsplash10-03di-2920000000-a4bb0f67851a49bcd19cSpectrum
GC-MSHexanedioic acid, non-derivatized, GC-MS Spectrumsplash10-0a6u-9000000000-36d8bc2f7d1a77a7b466Spectrum
GC-MSHexanedioic acid, non-derivatized, GC-MS Spectrumsplash10-03dm-0910000000-596aa8217b629d682b81Spectrum
GC-MSHexanedioic acid, non-derivatized, GC-MS Spectrumsplash10-03dj-0900000000-5378ec232b7bc8c84368Spectrum
GC-MSHexanedioic acid, non-derivatized, GC-MS Spectrumsplash10-03di-2920000000-a4bb0f67851a49bcd19cSpectrum
GC-MSHexanedioic acid, non-derivatized, GC-MS Spectrumsplash10-03dj-0900000000-60ba84e1d479d88e3facSpectrum
Predicted GC-MSHexanedioic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0fk9-9300000000-c0da1d9e52f67b1d7dbcSpectrum
Predicted GC-MSHexanedioic acid, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00dr-9620000000-9525dd4ed0f987b19a68Spectrum
Predicted GC-MSHexanedioic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSHexanedioic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSHexanedioic acid, TMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSHexanedioic acid, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSHexanedioic acid, TBDMS_2_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-000x-3900000000-1c5a6a5287f8fd7736f12012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-001i-9100000000-3e9496a6da881edd91e02012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-0uea-9500000000-edb5529010e4b88414c42012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - EI-B (Unknown) , Positivesplash10-0a6u-9000000000-36d8bc2f7d1a77a7b4662012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-0002-0900000000-a1852cfc66b4feae9b182012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-0ue9-6900000000-90e783cc3522f0ce78802012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-001i-9200000000-b5a64d560d8bc62d8d512012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-001i-9000000000-a96d5ee9551b944e4db82012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-001i-9000000000-2e61b7d2a4dbc98671232012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0002-0900000000-a1852cfc66b4feae9b182017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0ue9-6900000000-90e783cc3522f0ce78802017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-001i-9200000000-b5a64d560d8bc62d8d512017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-001i-9000000000-a96d5ee9551b944e4db82017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-001i-9000000000-2e61b7d2a4dbc98671232017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0002-2900000000-983aa19fb3183a9bc5ab2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-0ue9-8900000000-a976da84fb798bd80a342021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-0n33-9100000000-8ed018879ca3f86cd3792021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-9300000000-c6cf63d45cff0205c31a2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-001i-9200000000-9d33c5f6441e750719382021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004j-0900000000-ece39ae1f752cf2970f12017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0fba-5900000000-682fc79230e6f03bacfb2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-9000000000-66b61bf2c65c15bb7fed2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0900000000-ec5d2c95f1dac53496082017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-002b-2900000000-27613c7de7a721350bb82017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9100000000-78804e4122c63b62ca5b2017-09-01View Spectrum
NMR
TypeDescriptionView
1D NMR13C NMR Spectrum (1D, 125 MHz, H2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 90 MHz, DMSO-d6, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 15.08 MHz, DMSO-d6, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, experimental)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Spectrum
ChemSpider ID191
ChEMBL IDCHEMBL1157
KEGG Compound IDC06104
Pubchem Compound ID196
Pubchem Substance IDNot Available
ChEBI ID30832
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB00448
CRC / DFC (Dictionary of Food Compounds) IDDFV47-H:DFV47-H
EAFUS ID64
Dr. Duke IDADIPIC-ACID
BIGG IDNot Available
KNApSAcK IDC00001178
HET ID0L1
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDrw1001801
SuperScent IDNot Available
Wikipedia IDAdipic acid
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
acidulant64047 Any substance which is added to food to preserve or enhance its flavour and/or appearance.DUKE
irritantDUKE
perfumery48318 A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell.DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
odorless
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot 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).