Showing Compound Azelaic acid (FDB012192)

Record Information

Version

1.0

Creation date

2010-04-08 22:10:02 UTC

Update date

2025-11-18 23:34:44 UTC

Primary ID

FDB012192

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Azelaic acid

Description

Azelaic 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 Number

123-99-9

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
1,7-Dicarboxyheptane	ChEBI
1,7-Heptanedicarboxylic acid	ChEBI
1,9-Nonanedioic acid	ChEBI
Acide azelaique	ChEBI
Acidum azelaicum	ChEBI
Anchoic acid	ChEBI
Azelainsaeure	ChEBI
Azelex	ChEBI
Finacea	ChEBI
Lepargylic acid	ChEBI
N-Nonanedioic acid	ChEBI
Nonandisaeure	ChEBI
Skinoren	ChEBI
Nonanedioic acid	Kegg
1,7-Heptanedicarboxylate	Generator
1,9-Nonanedioate	Generator
Anchoate	Generator
Lepargylate	Generator
N-Nonanedioate	Generator
Nonanedioate	Generator
Azelaate	Generator
Azalaic acid	HMDB
Azelaicacidtech	HMDB
Azelainic acid	HMDB
Azelate	HMDB
Emerox 1110	HMDB
Emerox 1144	HMDB
Emery'S L-110	HMDB
Finevin	HMDB
Heptanedicarboxylic acid	HMDB
Nonanedioic acid azelaic acid	HMDB
Nonanedioic acid homopolymer	HMDB
Poly(azelaic anhydride)	HMDB
Polyazelaic anhydride	HMDB
Skinorem	HMDB
Azelaic acid, dilithium salt	HMDB
Azelaic acid, dipotassium salt	HMDB
Azelaic acid, disodium salt	HMDB
Azelaic acid, monosodium salt	HMDB
Azelaic acid, potassium salt	HMDB
Azelaic acid, sodium salt	HMDB
Monosodium azelate	HMDB
Azelaic acid	PhytoBank
Azelic acid	PhytoBank
alpha,omega-Nonanedioic acid	PhytoBank
α,ω-Nonanedioic acid	PhytoBank
1, 9-Nonanedioic acid	biospider
1tuf	biospider
Acido azelaico	biospider
Azelaic acid (usan/inn)	biospider
Azelaic acid [usan:inn]	biospider
Azelaic acid polyanhydride	biospider
AZELAIC ACID, 95%	biospider
Azelaic acid, INN, USAN	db_source
Azelaic polyanhydride	biospider
Azelex (TN)	biospider
Azleaic acid	biospider
Emery's L-110	biospider
Finacea (TN)	biospider
N-nonanedioate	biospider
N-nonanedioic acid	biospider
Nonanedioic acid, homopolymer	biospider
ZK 62498	db_source

Predicted Properties

Property	Value	Source
Water Solubility	2.28 g/L	ALOGPS
logP	1.37	ALOGPS
logP	1.82	ChemAxon
logS	-1.9	ALOGPS
pKa (Strongest Acidic)	4.15	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	8	ChemAxon
Refractivity	46.54 m³·mol⁻¹	ChemAxon
Polarizability	20.5 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C9H16O4

IUPAC name

nonanedioic acid

InChI Identifier

InChI=1S/C9H16O4/c10-8(11)6-4-2-1-3-5-7-9(12)13/h1-7H2,(H,10,11)(H,12,13)

InChI Key

BDJRBEYXGGNYIS-UHFFFAOYSA-N

Isomeric SMILES

OC(=O)CCCCCCCC(O)=O

Average Molecular Weight

188.2209

Monoisotopic Molecular Weight

188.104859

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.

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:48131 )
Dicarboxylic acids (C08261 )
Dicarboxylic acids (LMFA01170054 )

Ontology

Dermal

Enteral:

Ingestion

Source:

Synthetic:

Personal care product

Biological:

Plant:

Fabaceae

Biological location:

Subcellular:

Biofluid and excreta:

Organ and components:

Process

Naturally occurring process:

Biological process:

Biochemical process:

Biochemical pathway:

Lipid metabolism pathway

Chemical reaction:

Lipid peroxidation

Role

Biological role:

Industrial application:

Personal care products

Pharmaceutical industry:

Pharmaceutical

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Solid
Physical Description	Not Available
Mass Composition	C 57.43%; H 8.57%; O 34.00%	DFC
Melting Point	Mp 106.5°	DFC
Boiling Point	Bp10 226°	DFC
Experimental Water Solubility	2.4 mg/mL at 20 oC	YALKOWSKY,SH & HE,Y (2003)
Experimental logP	1.57	HANSCH,C ET AL. (1995)
Experimental pKa	pKa2 5.53 (25°, 0.1M KNO3)	DFC
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)	splash10-06rx-9100000000-6db2acb47ad4c6163063	2014-09-20	View Spectrum
GC-MS	Azelaic acid, 2 TMS, GC-MS Spectrum	splash10-0v0r-4920000000-5a3ed693b1c4083f1f15	Spectrum
GC-MS	Azelaic acid, non-derivatized, GC-MS Spectrum	splash10-0v0r-4920000000-5a3ed693b1c4083f1f15	Spectrum
GC-MS	Azelaic acid, non-derivatized, GC-MS Spectrum	splash10-00mk-1910000000-83ba58dac4b0698643d0	Spectrum
Predicted GC-MS	Azelaic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-000f-9600000000-24638c458fa83f47c259	Spectrum
Predicted GC-MS	Azelaic acid, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00y0-9740000000-d157d08c3a7c87244190	Spectrum
Predicted GC-MS	Azelaic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Azelaic acid, TMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Azelaic acid, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Azelaic acid, TBDMS_2_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)	splash10-000i-0900000000-a118e433f0bd27a95b89	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)	splash10-006t-9600000000-93b3a375b722791cb5c9	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)	splash10-052k-9500000000-6b069f2fed947651b284	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-000i-0900000000-7980b5eadcca6ee1eadd	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-004i-0900000000-462585874f7661d40d5b	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-004j-4900000000-0f65eeeed8c8a6ff3cc9	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-0002-9300000000-d654ca3c764066f98358	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-0002-9000000000-60a08bb384f2b4cbfca8	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-000i-0900000000-7980b5eadcca6ee1eadd	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-004i-0900000000-462585874f7661d40d5b	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-004j-4900000000-0f65eeeed8c8a6ff3cc9	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0002-9300000000-fcefbd80852c2625bc0e	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0002-9000000000-60a08bb384f2b4cbfca8	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-004i-0900000000-26216115e75cad833509	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-004i-0900000000-7bef8272c481ea57a60b	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-004i-0900000000-751bf479539d4bd2b5e1	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-00di-0900000000-9a056a45b27896966bf9	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-00di-0900000000-3155fd845eec8f32ce93	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - , negative	splash10-004r-0900000000-544110f97ebc0f97e15b	2017-09-14	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00dr-0900000000-b1b7c1ab57d58a2405a8	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00g3-2900000000-d0ba7fbbe987efa4c818	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-05qd-9100000000-8d65a19b998d18ad08ac	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0900000000-a7edc3ac66d27685b9d1	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00kr-1900000000-c56b9d972f88c58dc65b	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-9300000000-47cbefe19a788d7f36b9	2015-04-25	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 90 MHz, DMSO-d6, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 15.08 MHz, DMSO-d6, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CD₃OD, experimental)	Spectrum

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

48131

Phenol-Explorer ID

Not Available

DrugBank ID

DB00548

HMDB ID

HMDB00784

CRC / DFC (Dictionary of Food Compounds) ID

HDZ47-F:HDZ47-F

EAFUS ID

Not Available

Dr. Duke ID

NONANEDIOIC-ACID|AZELAIC-ACID

BIGG ID

Not Available

KNApSAcK ID

C00045634

HET ID

AZ1

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Nonanedioic 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
Anti-acne	50177	An agent that reduces acne symptoms, commonly used in managing acne vulgaris by minimizing oil production, preventing clogged pores, and decreasing bacterial growth, thereby reducing inflammation and promoting healthy skin.	DUKE
Anti hyperpigmentative	52217	An agent that reduces melanin production, used to treat hyperpigmentation disorders such as melasma, freckles, and age spots, promoting skin whitening and evening out skin tone.	DUKE
Anti leukemic	35610	An agent that targets and inhibits the growth of leukemia cells, playing a crucial role in cancer treatment. Therapeutically, it is used to induce remission, manage symptoms, and improve survival rates in patients with leukemia. Key medical uses include treating acute and chronic leukemia, lymphoma, and other hematological malignancies.	DUKE
Anti-melanomic	35610	An agent that inhibits melanin production, reducing melanoma cell growth. It has therapeutic applications in treating skin cancers, particularly melanoma, and key medical uses include preventing tumor progression and metastasis, as well as managing pigmentation disorders.	DUKE
Anti-melasmic		An agent that reduces melasma, a skin discoloration condition, by inhibiting melanin production. It is therapeutically used to treat hyperpigmentation, commonly occurring during pregnancy or hormonal changes, and has key medical applications in dermatology for skin whitening and brightening treatments.	DUKE
Anti-proliferative		An agent that inhibits cell growth and division, particularly in cancer cells, preventing tumor expansion. It plays a biological role in regulating cell cycles and has therapeutic applications in cancer treatment, such as chemotherapy and targeted therapy, with key medical uses in managing various types of cancer and other proliferative diseases.	DUKE
Antitumor	35610	An agent that inhibits tumor growth and proliferation, playing a crucial role in cancer treatment. Therapeutically, antitumors are used to manage various types of cancer, including chemotherapy, targeted therapy, and immunotherapy, helping to reduce tumor size, prevent metastasis, and improve patient outcomes.	DUKE
Cytotoxic	52209	An agent that kills or damages cells, playing a biological role in immune responses and therapeutic applications in cancer treatment. Key medical uses include chemotherapy, targeting and destroying cancer cells, and treating certain autoimmune diseases by eliminating harmful cells.	DUKE
Anti bacterial	33282	An agent that inhibits the growth of or destroys bacteria, playing a crucial role in preventing and treating infections. Therapeutically, it is used to combat bacterial infections, with key medical applications including treating pneumonia, tuberculosis, and skin infections, as well as preventing surgical site infections and sepsis.	CHEBI