Undecylenic acid
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Undecylenic acid
structure -
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CAS No:
112-38-9
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Formula:
C11H20O2
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Chemical Name:
Undecylenic acid
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Synonyms:
10-Undecenoic acid;Declid;10-Hendecenoic acid;ω-Hendecenoic acid;Renselin;Sevinon;10-Undecylenic acid;Undecylenic acid;Desenex solution;ω-Undecenoic acid;NSC 2013;949900-17-8
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CAS No:
Description
10-Undecenoic acid was used as a starting reagent in the syntheses of Pheromone (11Z)-hexadecenal.
Liquid|Solid|colourless to pale yellow liquid
10-undecenoic acid is an undecenoic acid having its double bond in the 10-position. It is derived from castor oil and is used for the treatment of skin problems. It has a role as a plant metabolite and an antifungal drug. It is a conjugate acid of a 10-undecenoate.|Undecylenate, or undecylenic acid, is an unsaturated fatty acid with a terminal double bond that is derived from castor oil. Undecylenic acid is also found naturally in the human sweat. It is used as a precursor in the manufacture of aromatic chemicals, polymers or modified silicones. Undecylenic acid was first isolated from the products of distillation of castor oil in 1877 via pyrolysis of ricinoleic acid, and has been polymerized for vinyl production. It it suggested that many organic fatty acids exert fungicidal or fungistatic actions. Undecylenic acid also possesses antifungal properties, but is never used on its own for antifungal purposes. Salts of undecylenate are found in topical over-the-counter or mixture products as antifungal agents. Zinc undecylenate is an example of a topical antifungal agent that treats skin infections such as athlete’s foot and relieves itching, burning, and irritation associated with the skin condition. Due to its bifunctional properties, undecylenate is also used as a linking molecule to conjugate other biomolecules such as proteins. It serves as an acid moiety for anabolic steroid boldenone.|Undecylenic Acid is a natural or synthetic fungistatic fatty acid, antifungal Undecylenic Acid is used topically as a zinc salt in various creams against fungal infections, eczemas, ringworm, and other cutaneous conditions. The zinc provides an astringent action, reducing rawness and irritation.
Undecylenic acid Basic Attributes
184.28
184.28
1762631
203-965-8
K3D86KJ24N
759153|2013
DTXSID8035001
C29530
D - Dermatologicals
2916190090
Characteristics
37.3
3.86
Pale yellow Crystalline Low Melting Solid or Liquid
0.912 g/mL at 25 °C(lit.)
24.5 °C
275 °C
300 °F
n20/D 1.449(lit.)
H2O: INsoluble
-20°C
9.37e-04 mmHg
Safety Information
UN 3261 8/PG 2
1
36/37/38-52/53-36/38
26-61-37/39-36
YQ2975000
Xi
P261-P273-P305 + P351 + P338
H315-H319-H335-H412
|Warning|H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]|P264, P273, P280, P302+P352, P305+P351+P338, P321, P332+P313, P337+P313, P362, and P501|Aggregated GHS information provided by 1789 companies from 14 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Toxicity
Acute oral LD50 in rat and mouse are 2500 mg/kg and 8150 mg/kg, respectively [MSDS]. Acute dermal LD50 in guinea pig and rat are 50 mg/kg and 2000 mg/kg, respectively [MSDS]. There are no data available on the carcinogenicity, mutagenicity, teratogenicity and developmental toxicity of undecylenate [MSDS]. Oral overdosage may lead to gastrointestinal disturbances, and may affect central nervous system (excitement, somnolence, muscle contraction or spasticity, headache, dizziness), and metabolism (loss of appetite). Prolonged or repeated exposure to undecylenate may cause anorexia or weight loss [MSDS].
No information regarding protein binding.
Drug Information
Indicated for the treatment of fungal infections as a salt form. No therapeutic indications on its own.
Zinc undecylendate acts as a fungistatic agent but fungicidal activity may be observed with chronic exposure in high concentrations. It is effective against _Candida albicans_. It is proposed that undecylenic acid exerts antimicrobial actions via interacting with nonspecific components in the cell membrane.
Undecylenic acid may be absorbed through the skin [MSDS].|No information regarding route of elimination.|No information regarding volume of distribution.|No information regarding clearance.
No information regarding metabolism.
No information regarding half-life.
Undecylenic acid demonstrated effectiveness against _Candida albicans_, which is an opportunistic pathogenic yeast with two cellular morphologies: the round yeast form and the filamentous form with elongated hyphae. Hyphae formation is associated with active infections and virulence. A study proposed that undecylenic acid inhibits biofilm formation of _Candida albicans_ with optimal concentration above 3 mM and disrupts hyphal growth, which is the morphological transition from yeast to filamentous phase, at concentration above 4 mM. Under the drug treatment, hyphal formation related genes, like HWP1, were significantly reduced in transcriptional level leading to poor biofilm formation. Both biofilm and hyphae formation are critical virulence factors for the initiation of skin infection and late development of disseminated infection. Undecylenic acid may also inhibit enzyme involved in lipid metabolism and abolish germ tube formation by carrying protons across the plasma membrane, thus altering cytoplasmic pH.
10-undecenoic acid
Undecylenic acid Use and Manufacturing
used as antifoaming and surface active agent. As its sulfo – succinate derivative it is used in anti-dandruff shampoos
Intermediates
All other basic organic chemical manufacturing|10-Undecenoic acid: ACTIVE
EPA Safer Chemical Functional Use Classes -> Preservatives and Antioxidants|Safer Chemical Classes -> Yellow triangle - The chemical has met Safer Choice Criteria for its functional ingredient-class, but has some hazard profile issues|Food additives -> Flavoring Agents|Flavoring Agents -> JECFA Flavorings Index|Fatty Acyls [FA] -> Fatty Acids and Conjugates [FA01] -> Unsaturated fatty acids [FA0103]|Cosmetics -> Cleansing; Preservative
Flavoring Agents
Computed Properties
Molecular Weight:184.27
XLogP3:3.9
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:9
Exact Mass:184.146329876
Monoisotopic Mass:184.146329876
Topological Polar Surface Area:37.3
Heavy Atom Count:13
Complexity:141
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
Drug Function and Efficacy
Antifungal drugs have strong fungus inhibition function and certain antipruritic and anti-allergic effects
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