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Azelaic acid (FDB012192)

Record Information
Version1.0
Creation date2010-04-08 22:10:02 UTC
Update date2020-09-17 15:33:19 UTC
Primary IDFDB012192
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameAzelaic acid
DescriptionAzelaic acid, also known as 1,9-nonanedioate, AZA or azelex, is a saturated nine-carbon dicarboxylic acid. It ocurrs in all living organisms, ranging from bacteria to humans. AZA possesses a variety of in vitro and in vivo biological activities. In aerobic bacteria, azelaic acid reversibly inhibits several oxidoreductive enzymes including tyrosinase, mitochondrial enzymes of the respiratory chain, thioredoxin reductase, 5-alpha-reductase, and DNA polymerases. It is currently used as a topical treatment of mild to moderate inflammatory acne vulgaris, due to its antibiotic effects on skin bacteria. Its effectiveness is similar to that of other agents without the systemic side effects of oral antibiotics or the allergic sensitization of topical benzoyl peroxide and with less irritation than tretinoin. Azelaic acid is less expensive than certain other prescription acne preparations, but it is much more expensive than nonprescription benzoyl peroxide preparations. Whether it is safe and effective when used in combination with other agents is not known. (PMID: 7737781, 8961845). In plants, azelaic acid serves as a "distress flare" involved in defense responses after infection. It serves as a signal that induces the accumulation of salicylic acid, an important component of the plants defensive response (PMID: 19342588). AZA is found in high abundance in several crop plants including wheat, rye, and barley. Azelaic acid has been detected, but not quantified in, a few different foods, such as asparagus, common beans, and potato. This could make azelaic acid a potential biomarker for the consumption of these foods. Azelaic acid is a precursor to a number of industrial products including polymers and plasticizers, as well as being a component of a number of hair and skin conditioners.
CAS Number123-99-9
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
Not AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility2.28 g/LALOGPS
logP1.37ALOGPS
logP1.82ChemAxon
logS-1.9ALOGPS
pKa (Strongest Acidic)4.15ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area74.6 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity46.54 m³·mol⁻¹ChemAxon
Polarizability20.5 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC9H16O4
IUPAC namenonanedioic acid
InChI IdentifierInChI=1S/C9H16O4/c10-8(11)6-4-2-1-3-5-7-9(12)13/h1-7H2,(H,10,11)(H,12,13)
InChI KeyBDJRBEYXGGNYIS-UHFFFAOYSA-N
Isomeric SMILESOC(=O)CCCCCCCC(O)=O
Average Molecular Weight188.2209
Monoisotopic Molecular Weight188.104859
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

Biological role:

Industrial application:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 57.43%; H 8.57%; O 34.00%DFC
Melting PointMp 106.5°DFC
Boiling PointBp10 226°DFC
Experimental Water Solubility2.4 mg/mL at 20 oCYALKOWSKY,SH & HE,Y (2003)
Experimental logP1.57HANSCH,C ET AL. (1995)
Experimental pKapKa2 5.53 (25°, 0.1M KNO3)DFC
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)splash10-06rx-9100000000-6db2acb47ad4c61630632014-09-20View Spectrum
GC-MSAzelaic acid, 2 TMS, GC-MS Spectrumsplash10-0v0r-4920000000-5a3ed693b1c4083f1f15Spectrum
GC-MSAzelaic acid, non-derivatized, GC-MS Spectrumsplash10-0v0r-4920000000-5a3ed693b1c4083f1f15Spectrum
GC-MSAzelaic acid, non-derivatized, GC-MS Spectrumsplash10-00mk-1910000000-83ba58dac4b0698643d0Spectrum
Predicted GC-MSAzelaic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-000f-9600000000-24638c458fa83f47c259Spectrum
Predicted GC-MSAzelaic acid, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00y0-9740000000-d157d08c3a7c87244190Spectrum
Predicted GC-MSAzelaic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSAzelaic acid, TMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSAzelaic acid, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSAzelaic 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)splash10-000i-0900000000-a118e433f0bd27a95b892012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-006t-9600000000-93b3a375b722791cb5c92012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-052k-9500000000-6b069f2fed947651b2842012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-000i-0900000000-7980b5eadcca6ee1eadd2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-004i-0900000000-462585874f7661d40d5b2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-004j-4900000000-0f65eeeed8c8a6ff3cc92012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-0002-9300000000-d654ca3c764066f983582012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-0002-9000000000-60a08bb384f2b4cbfca82012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000i-0900000000-7980b5eadcca6ee1eadd2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-0900000000-462585874f7661d40d5b2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004j-4900000000-0f65eeeed8c8a6ff3cc92017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0002-9300000000-fcefbd80852c2625bc0e2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0002-9000000000-60a08bb384f2b4cbfca82017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-004i-0900000000-26216115e75cad8335092017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-004i-0900000000-7bef8272c481ea57a60b2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-004i-0900000000-751bf479539d4bd2b5e12017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-00di-0900000000-9a056a45b27896966bf92017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-00di-0900000000-3155fd845eec8f32ce932017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - , negativesplash10-004r-0900000000-544110f97ebc0f97e15b2017-09-14View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00dr-0900000000-b1b7c1ab57d58a2405a82015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00g3-2900000000-d0ba7fbbe987efa4c8182015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05qd-9100000000-8d65a19b998d18ad08ac2015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0900000000-a7edc3ac66d27685b9d12015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00kr-1900000000-c56b9d972f88c58dc65b2015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9300000000-47cbefe19a788d7f36b92015-04-25View Spectrum
NMR
TypeDescriptionView
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 NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CD3OD, experimental)Spectrum
ChemSpider ID2179
ChEMBL IDCHEMBL1238
KEGG Compound IDC08261
Pubchem Compound ID2266
Pubchem Substance IDNot Available
ChEBI ID48131
Phenol-Explorer IDNot Available
DrugBank IDDB00548
HMDB IDHMDB00784
CRC / DFC (Dictionary of Food Compounds) IDHDZ47-F:HDZ47-F
EAFUS IDNot Available
Dr. Duke IDNONANEDIOIC-ACID|AZELAIC-ACID
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDAZ1
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNonanedioic 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
anti acne50177 A drug used to treat or prevent skin disorders or for the routine care of skin.DUKE
anti hyperpigmentative52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti leukemic35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
anti melanomic35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
anti melasmicDUKE
anti proliferativeDUKE
antitumor35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
cytotoxic52209 A role played by the molecular entity or part thereof which causes the development of a pathological process.DUKE
anti bacterial33282 A substance that kills or slows the growth of bacteria.CHEBI
Enzymes
NameGene NameUniProt ID
3-oxo-5-beta-steroid 4-dehydrogenaseAKR1D1P51857
3-oxo-5-alpha-steroid 4-dehydrogenase 2SRD5A2P31213
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).