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
Synonyms
SynonymSource
1,7-DicarboxyheptaneChEBI
1,7-Heptanedicarboxylic acidChEBI
1,9-Nonanedioic acidChEBI
Acide azelaiqueChEBI
Acidum azelaicumChEBI
Anchoic acidChEBI
AzelainsaeureChEBI
AzelexChEBI
FinaceaChEBI
Lepargylic acidChEBI
N-Nonanedioic acidChEBI
NonandisaeureChEBI
SkinorenChEBI
Nonanedioic acidKegg
1,7-HeptanedicarboxylateGenerator
1,9-NonanedioateGenerator
AnchoateGenerator
LepargylateGenerator
N-NonanedioateGenerator
NonanedioateGenerator
AzelaateGenerator
Azalaic acidHMDB
AzelaicacidtechHMDB
Azelainic acidHMDB
AzelateHMDB
Emerox 1110HMDB
Emerox 1144HMDB
Emery'S L-110HMDB
FinevinHMDB
Heptanedicarboxylic acidHMDB
Nonanedioic acid azelaic acidHMDB
Nonanedioic acid homopolymerHMDB
Poly(azelaic anhydride)HMDB
Polyazelaic anhydrideHMDB
SkinoremHMDB
Azelaic acid, dilithium saltHMDB
Azelaic acid, dipotassium saltHMDB
Azelaic acid, disodium saltHMDB
Azelaic acid, monosodium saltHMDB
Azelaic acid, potassium saltHMDB
Azelaic acid, sodium saltHMDB
Monosodium azelateHMDB
Azelaic acidPhytoBank
Azelic acidPhytoBank
alpha,omega-Nonanedioic acidPhytoBank
α,ω-Nonanedioic acidPhytoBank
1, 9-Nonanedioic acidbiospider
1tufbiospider
Acido azelaicobiospider
Azelaic acid (usan/inn)biospider
Azelaic acid [usan:inn]biospider
Azelaic acid polyanhydridebiospider
AZELAIC ACID, 95%biospider
Azelaic acid, INN, USANdb_source
Azelaic polyanhydridebiospider
Azelex (TN)biospider
Azleaic acidbiospider
Emery's L-110biospider
Finacea (TN)biospider
N-nonanedioatebiospider
N-nonanedioic acidbiospider
Nonanedioic acid, homopolymerbiospider
ZK 62498db_source
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 - Experimental
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-9100000000-6db2acb47ad4c6163063Spectrum
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
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-000i-0900000000-a118e433f0bd27a95b89Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-006t-9600000000-93b3a375b722791cb5c9Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-052k-9500000000-6b069f2fed947651b284Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-000i-0900000000-7980b5eadcca6ee1eaddSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-004i-0900000000-462585874f7661d40d5bSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-004j-4900000000-0f65eeeed8c8a6ff3cc9Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-0002-9300000000-d654ca3c764066f98358Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-0002-9000000000-60a08bb384f2b4cbfca8Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000i-0900000000-7980b5eadcca6ee1eaddSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-0900000000-462585874f7661d40d5bSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004j-4900000000-0f65eeeed8c8a6ff3cc9Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0002-9300000000-fcefbd80852c2625bc0eSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0002-9000000000-60a08bb384f2b4cbfca8Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-004i-0900000000-26216115e75cad833509Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-004i-0900000000-7bef8272c481ea57a60bSpectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-004i-0900000000-751bf479539d4bd2b5e1Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-00di-0900000000-9a056a45b27896966bf9Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-00di-0900000000-3155fd845eec8f32ce93Spectrum
MS/MSLC-MS/MS Spectrum - , negativesplash10-004r-0900000000-544110f97ebc0f97e15bSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00dr-0900000000-b1b7c1ab57d58a2405a8Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00g3-2900000000-d0ba7fbbe987efa4c818Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05qd-9100000000-8d65a19b998d18ad08acSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0900000000-a7edc3ac66d27685b9d1Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00kr-1900000000-c56b9d972f88c58dc65bSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9300000000-47cbefe19a788d7f36b9Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
2D NMR[1H,13C] 2D NMR SpectrumSpectrum
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).