Record Information
Version1.0
Creation date2010-04-08 22:10:02 UTC
Update date2015-10-09 22:28:25 UTC
Primary IDFDB012192
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameAzelaic acid
DescriptionOccurs in rancid fats. Isol. from a few higher plants Azelaic acid (AZA) is a naturally occurring saturated nine-carbon dicarboxylic acid (COOH (CH2)7-COOH). It possesses a variety of biological actions both in vitro and in vivo. Interest in the biological activity of AZA arose originally out of studies of skin surface lipids and the pathogenesis of hypochromia in pityriasis versicolor infection. Later, it was shown that Pityrosporum can oxidize unsaturated fatty acids to C8-C12 dicarboxylic acids that are cornpetitive inhibitors of tyrosinase in vitro. Azelaic acid was chosen for further investigation and development of a new topical drug for treating hyperpigmentary disorders for the following reasons: it possesses a middle-range of antityrosinase activity, is inexpensive, and more soluble to be incorporated into a base cream than other dicarboxylic acids. Azelaic acid is another option for the topical treatment of mild to moderate inflammatory acne vulgaris. It offers effectiveness 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); Azelaic acid is a saturated dicarboxylic acid found naturally in wheat, rye, and barley. It is a natural substance that is produced by Malassezia furfur (also known as Pityrosporum ovale), a yeast that lives on normal skin. It is effective against a number of skin conditions, such as mild to moderate acne, when applied topically in a cream formulation of 20%. It works in part by stopping the growth of skin bacteria that cause acne, and by keeping skin pores clear. Azelaic acid's antimicrobial action may be attributable to inhibition of microbial cellular protein synthesis.; Azelaic acid is a saturated dicarboxylic acid found naturally in wheat, rye, and barley. It is a natural substance that is produced by Malassezia furfur (also known as Pityrosporum ovale), a yeast that lives on normal skin. It is effective against a number of skin conditions, such as mild to moderate acne, when applied topically in a cream formulation of 20%. Azelaic acid may be useful as a hair growth stimulant.[citation needed]
CAS Number123-99-9
Structure
Thumb
Synonyms
SynonymSource
1, 9-Nonanedioic acidbiospider
1,7-Dicarboxyheptanebiospider
1,7-Heptanedicarboxylatebiospider
1,7-Heptanedicarboxylic aciddb_source
1,9-Nonanedioatebiospider
1,9-Nonanedioic acidbiospider
1tufbiospider
Acide azelaiqueChEBI
Acido azelaicobiospider
Acidum azelaicumbiospider
Anchoatebiospider
Anchoic aciddb_source
Azalaic acidbiospider
AzelaateGenerator
Azelaic acidbiospider
Azelaic acid (usan/inn)biospider
Azelaic acid [usan:inn]biospider
Azelaic acid polyanhydridebiospider
AZELAIC ACID, 95%biospider
Azelaic acid, INN, USANdb_source
Azelaic polyanhydridebiospider
Azelaicacidtechbiospider
Azelainic acidbiospider
AzelainsaeureChEBI
Azelatebiospider
Azelexbiospider
Azelex (TN)biospider
Azleaic acidbiospider
Emerox 1110biospider
Emerox 1144db_source
Emery's L-110biospider
Finaceabiospider
Finacea (TN)biospider
Finevinbiospider
Heptanedicarboxylic acidbiospider
Lepargylatebiospider
Lepargylic aciddb_source
N-nonanedioatebiospider
N-nonanedioic acidbiospider
NonandisaeureChEBI
Nonanedioatebiospider
Nonanedioic acidChEBI
Nonanedioic acid azelaic acidbiospider
Nonanedioic acid homopolymerbiospider
Nonanedioic acid, homopolymerbiospider
Poly(azelaic anhydride)biospider
Polyazelaic anhydridebiospider
Skinorembiospider
Skinorendb_source
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
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 KeyInChIKey=BDJRBEYXGGNYIS-UHFFFAOYSA-N
Isomeric SMILESOC(=O)CCCCCCCC(O)=O
Average Molecular Weight188
Monoisotopic Molecular Weight188
Classification
DescriptionThis compound 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
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
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-0v0r-4920000000-5a3ed693b1c4083f1f15View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0v0r-4920000000-5a3ed693b1c4083f1f15View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00mk-1910000000-83ba58dac4b0698643d0View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000f-9600000000-24638c458fa83f47c259View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00y0-9740000000-d157d08c3a7c87244190View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-000i-0900000000-a118e433f0bd27a95b89View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-006t-9600000000-93b3a375b722791cb5c9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-052k-9500000000-6b069f2fed947651b284View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-000i-0900000000-7980b5eadcca6ee1eaddView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-004i-0900000000-462585874f7661d40d5bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-004j-4900000000-0f65eeeed8c8a6ff3cc9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-0002-9300000000-d654ca3c764066f98358View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-0002-9000000000-60a08bb384f2b4cbfca8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000i-0900000000-7980b5eadcca6ee1eaddView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-0900000000-462585874f7661d40d5bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004j-4900000000-0f65eeeed8c8a6ff3cc9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0002-9300000000-fcefbd80852c2625bc0eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0002-9000000000-60a08bb384f2b4cbfca8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-004i-0900000000-26216115e75cad833509View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-004i-0900000000-7bef8272c481ea57a60bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-004i-0900000000-751bf479539d4bd2b5e1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-00di-0900000000-9a056a45b27896966bf9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-00di-0900000000-3155fd845eec8f32ce93View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , negativesplash10-004r-0900000000-544110f97ebc0f97e15bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00dr-0900000000-b1b7c1ab57d58a2405a8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00g3-2900000000-d0ba7fbbe987efa4c818View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05qd-9100000000-8d65a19b998d18ad08acView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0900000000-a7edc3ac66d27685b9d1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00kr-1900000000-c56b9d972f88c58dc65bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9300000000-47cbefe19a788d7f36b9View in MoNA
MSMass Spectrum (Electron Ionization)splash10-06rx-9100000000-6db2acb47ad4c6163063View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
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
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).