Azelaic acid
Encyclopedia
Azelaic acid is an organic compound
with the formula (CH2)7(CO2H)2. This saturated dicarboxylic acid
exists as a white powder. It is found in wheat
, rye
, and barley
. It is a component of a number of hair and skin conditioners.
of oleic acid
. The side product is nonanoic acid. It is produced naturally by Malassezia furfur
(also known as Pityrosporum ovale), a yeast
that lives on normal skin
. The bacterial degradation of nonanoic acid gives azelaic acid
.
, an important component of a plant's defensive response.
-6,9, which finds specialized uses as a plastic.
, due to its ability to reduce inflammation. In some cases, females have reported hair growth on face and neck.
(HQ), the current gold standard for skin lightening, as countries such as Japan and the EU have questioned the safety of HQ.
It is a Tyrosinase
inhibitor. This reduces synthesis of melanin
.
ion
and vitamin B6
) was a strong type I 5-alpha reductase
(5-AR) inhibitor. The enzyme
, 5-AR (both Types I and II) convert testosterone
to dihydrotestosterone
(DHT). DHT has been shown to contribute to prostate enlargement (benign prostatic hyperplasia
, BPH) and to damage hair follicle
s. However, no clinical studies have confirmed its efficacy in helping with hair loss.
), Azelex (20% cream, Allergan
), White Action cream (20% cream,2% glycolic acid), SynCare), Finacea (15% gel, Intendis/Berlex Laboratories, subsidiaries of Bayer
AG), Finevin (20% cream, Intendis/Berlex Laboratories), Skinoren (20% cream or 15% gel, Intendis), and Azaclear (azelaic acid and niacinamide, Epikinetics LLC).
Organic compound
An organic compound is any member of a large class of gaseous, liquid, or solid chemical compounds whose molecules contain carbon. For historical reasons discussed below, a few types of carbon-containing compounds such as carbides, carbonates, simple oxides of carbon, and cyanides, as well as the...
with the formula (CH2)7(CO2H)2. This saturated dicarboxylic acid
Dicarboxylic acid
Dicarboxylic acids are organic compounds that contain two carboxylic acid functional groups. In molecular formulae for dicarboxylic acids, these groups are often written as HOOC-R-COOH, where R may be an alkyl, alkenyl, alkynyl, or aryl group...
exists as a white powder. It is found in wheat
Wheat
Wheat is a cereal grain, originally from the Levant region of the Near East, but now cultivated worldwide. In 2007 world production of wheat was 607 million tons, making it the third most-produced cereal after maize and rice...
, rye
Rye
Rye is a grass grown extensively as a grain and as a forage crop. It is a member of the wheat tribe and is closely related to barley and wheat. Rye grain is used for flour, rye bread, rye beer, some whiskeys, some vodkas, and animal fodder...
, and barley
Barley
Barley is a major cereal grain, a member of the grass family. It serves as a major animal fodder, as a base malt for beer and certain distilled beverages, and as a component of various health foods...
. It is a component of a number of hair and skin conditioners.
Production
Azelaic acid is industrially produced by the ozonolysisOzonolysis
Ozonolysis is the cleavage of an alkene or alkyne with ozone to form organic compounds in which the multiple carbon–carbon bond has been replaced by a double bond to oxygen...
of oleic acid
Oleic acid
Oleic acid is a monounsaturated omega-9 fatty acid found in various animal and vegetable fats. It has the formula CH37CH=CH7COOH. It is an odorless, colourless oil, although commercial samples may be yellowish. The trans isomer of oleic acid is called elaidic acid...
. The side product is nonanoic acid. It is produced naturally by Malassezia furfur
Malassezia furfur
Malassezia is a genus of fungi. Malassezia is naturally found on the skin surfaces of many animals, including humans. In occasional opportunistic infections,...
(also known as Pityrosporum ovale), a yeast
Yeast
Yeasts are eukaryotic micro-organisms classified in the kingdom Fungi, with 1,500 species currently described estimated to be only 1% of all fungal species. Most reproduce asexually by mitosis, and many do so by an asymmetric division process called budding...
that lives on normal skin
Skin
-Dermis:The dermis is the layer of skin beneath the epidermis that consists of connective tissue and cushions the body from stress and strain. The dermis is tightly connected to the epidermis by a basement membrane. It also harbors many Mechanoreceptors that provide the sense of touch and heat...
. The bacterial degradation of nonanoic acid gives azelaic acid
Azelaic acid
Azelaic acid is an organic compound with the formula 72. This saturated dicarboxylic acid exists as a white powder. It is found in wheat, rye, and barley. It is a component of a number of hair and skin conditioners.-Production:...
.
Biological function
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 acidSalicylic acid
Salicylic acid is a monohydroxybenzoic acid, a type of phenolic acid and a beta hydroxy acid. This colorless crystalline organic acid is widely used in organic synthesis and functions as a plant hormone. It is derived from the metabolism of salicin...
, an important component of a plant's defensive response.
Polymers and related materials
Esters of this dicarboxylic acid find applications in lubrication and plasticizers. With hexamethylenediamine azelaic acid forms NylonNylon
Nylon is a generic designation for a family of synthetic polymers known generically as polyamides, first produced on February 28, 1935, by Wallace Carothers at DuPont's research facility at the DuPont Experimental Station...
-6,9, which finds specialized uses as a plastic.
Acne treatment
Azelaic acid is used to treat mild to moderate acne; i.e. both comedonal acne and inflammatory acne. It works in part by stopping the growth of skin bacteria that cause acne, and by keeping skin pores clear.Rosacea treatment
Azelaic acid is also used as a topical gel treatment for rosaceaRosacea
Rosacea is a chronic condition characterized by facial erythema . Pimples are sometimes included as part of the definition. Unless it affects the eyes, it is typically a harmless cosmetic condition...
, due to its ability to reduce inflammation. In some cases, females have reported hair growth on face and neck.
Pigmentation treatment
Azelaic acid has been used for treatment of skin pigmentation including melasma and post inflammatory hyperpigmentation, particularly in those with darker skin types. It has been recommended as an alternative to hydroquinoneHydroquinone
Hydroquinone, also benzene-1,4-diol or quinol, is an aromatic organic compound that is a type of phenol, having the chemical formula C6H42. Its chemical structure, shown in the table at right, has two hydroxyl groups bonded to a benzene ring in a para position. It is a white granular solid...
(HQ), the current gold standard for skin lightening, as countries such as Japan and the EU have questioned the safety of HQ.
It is a Tyrosinase
Tyrosinase
Tyrosinase also known as monophenol monooxygenase is an enzyme that catalyses the oxidation of phenols and is widespread in plants and animals...
inhibitor. This reduces synthesis of melanin
Melanin
Melanin is a pigment that is ubiquitous in nature, being found in most organisms . In animals melanin pigments are derivatives of the amino acid tyrosine. The most common form of biological melanin is eumelanin, a brown-black polymer of dihydroxyindole carboxylic acids, and their reduced forms...
.
Hair loss
Azelaic acid may be useful as a hair growth stimulant. A research report by Stamatiadis in 1988 suggested that azelaic acid (and combinations of it, with zincZinc
Zinc , or spelter , is a metallic chemical element; it has the symbol Zn and atomic number 30. It is the first element in group 12 of the periodic table. Zinc is, in some respects, chemically similar to magnesium, because its ion is of similar size and its only common oxidation state is +2...
ion
Ion
An ion is an atom or molecule in which the total number of electrons is not equal to the total number of protons, giving it a net positive or negative electrical charge. The name was given by physicist Michael Faraday for the substances that allow a current to pass between electrodes in a...
and vitamin B6
Vitamin B6
Vitamin B6 is a water-soluble vitamin and is part of the vitamin B complex group. Several forms of the vitamin are known, but pyridoxal phosphate is the active form and is a cofactor in many reactions of amino acid metabolism, including transamination, deamination, and decarboxylation...
) was a strong type I 5-alpha reductase
5-alpha reductase
5α-reductases, also known as 3-oxo-5α-steroid 4-dehydrogenases, are enzymes involved in steroid metabolism. They participate in 3 metabolic pathways: bile acid biosynthesis, androgen and estrogen metabolism, and prostate cancer....
(5-AR) inhibitor. The enzyme
Enzyme
Enzymes are proteins that catalyze chemical reactions. In enzymatic reactions, the molecules at the beginning of the process, called substrates, are converted into different molecules, called products. Almost all chemical reactions in a biological cell need enzymes in order to occur at rates...
, 5-AR (both Types I and II) convert testosterone
Testosterone
Testosterone is a steroid hormone from the androgen group and is found in mammals, reptiles, birds, and other vertebrates. In mammals, testosterone is primarily secreted in the testes of males and the ovaries of females, although small amounts are also secreted by the adrenal glands...
to dihydrotestosterone
Dihydrotestosterone
Dihydrotestosterone is an androgen or male sex hormone. The enzyme 5α-reductase synthesises DHT in the prostate, testes, hair follicles, and adrenal glands...
(DHT). DHT has been shown to contribute to prostate enlargement (benign prostatic hyperplasia
Benign prostatic hyperplasia
Benign prostatic hyperplasia also known as benign prostatic hypertrophy , benign enlargement of the prostate , and adenofibromyomatous hyperplasia, refers to the increase in size of the prostate....
, BPH) and to damage hair follicle
Hair follicle
A hair follicle is a skin organ that produces hair. Hair production occurs in phases, including a growth phase , and cessation phase , and a rest phase . Stem cells are principally responsible for the production of hair....
s. However, no clinical studies have confirmed its efficacy in helping with hair loss.
Brand names
AzClear Action (20% lotion, Ego PharmaceuticalsEgo Pharmaceuticals
Ego Pharmaceuticals is a privately-held Australian pharmaceutical company with subsidiaries in Malaysia, Singapore and the United Kingdom, as well as staff in Bahrain, Kuwait, Qatar, United Arab Emirates and Saudi Arabia...
), Azelex (20% cream, Allergan
Allergan
Allergan, Inc., is a global specialty pharmaceutical company. Their product ranges include ophthalmic pharmaceuticals, dermatology products, and neurological products.-Profile:...
), White Action cream (20% cream,2% glycolic acid), SynCare), Finacea (15% gel, Intendis/Berlex Laboratories, subsidiaries of Bayer
Bayer
Bayer AG is a chemical and pharmaceutical company founded in Barmen , Germany in 1863. It is headquartered in Leverkusen, North Rhine-Westphalia, Germany and well known for its original brand of aspirin.-History:...
AG), Finevin (20% cream, Intendis/Berlex Laboratories), Skinoren (20% cream or 15% gel, Intendis), and Azaclear (azelaic acid and niacinamide, Epikinetics LLC).