10-ウンデセン酸
Undecylenic Acid
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基本情報
- CAS
112-38-9- 標準SMILES
C=CCCCCCCCCC(=O)O- InChIKey
FRPZMMHWLSIFAZ-UHFFFAOYSA-N- 分子式
- C11H20O2
- 平均分子量
- 184.27 g/mol
- 単同位体質量
- 184.14632988
概要
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.
名称と識別子
- 優先名称
- Undecylenic Acid
- IUPAC
- undec-10-enoic acid
- 現地名
- 10-ウンデセン酸
- 英語名
- Undecenoic acid
- 分子式
- C11H20O2
- 分子量
- 184.28
名称と別名
undecylenic acid10-UNDECENOIC ACIDUndec-10-enoic acid112-38-910-Hendecenoic acidRenselinSevinonDeclid10-Undecylenic acidundecylenateKyselina undecylenovaFEMA No. 3247
名称をさらに表示
10-ウンデセン酸デクリッドウンデシレン酸デセネックス溶液10-ヘンデセン酸デクリドセビノン10-ウンデシレン酸レンセリンデセネックス10ウンデシレン酸ウンデカ-10-エン酸10‐ウンデセン酸ウンデス-10-エン酸ウンデシレン酸 (JAN)FEMA 3247undecylenic9-Undecenoic acidundecyl-10-enicacidUndecenoic
UNDECEN-10-ACID-1omega-undecenoic acidomega-hendecenoic acidDTXSID8035001NSC-2013K3D86KJ24NCHEBI:35045NSC2013
データベース識別子
- CAS
112-38-9、1333-28-4、96451-28-4- PubChem CID
- 5634
- DTXSID
DTXSID8035001- ChEMBL
CHEMBL1276010- ChEBI
CHEBI:35045- UNII
- K3D86KJ24N
- EC Number
- 203-965-8、215-583-9、619-214-6
- Nikkaji
- J5.125J
物性
構造計算による物性補完中
- XLogP
- 3.9
- 極性表面積
- 37.3 Ų
- 水素結合供与体数
- 1
- 水素結合受容体数
- 2
- 回転可能結合数
- 9
- 重原子数
- 13
- 形式電荷
- 0
- 複雑度
- 141
実験および物理化学的性質
Chemical ClassesOther Classes -> Organic Acids
LipidsFatty Acyls [FA] -> Fatty Acids and Conjugates [FA01] -> Unsaturated fatty acids [FA0103]
Cosmetics
Cosmetic ingredients (Undecylenic Acid) -> CIR (Cosmetic Ingredient Review)
Preservative; Cleansing
SpringerMaterials PropertiesBoiling point
FragrancesFragrance Ingredient (10-Undecenoic acid) -> IFRA transparency List
LogP
3.86
3.86
Food AdditivesFLAVORING AGENT OR ADJUVANT -> FDA Substance added to food
Density0.910 - 0.917
Flavoring AgentsEU Flavoring substances
Solubility
Insoluble
0.0737 mg/mL at 30 °C
insoluble in water; soluble in alcohol and ether
(in ethanol)
安全と法規制
安全情報は参考情報です。供給元の安全データシート（SDS）、適用法令、専門家による評価に代わるものではありません。
GHS分類
GHS Classification
Warning
H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
P264, P264+P265, P273, P280, P302+P352, P305+P351+P338, P321, P332+P317, P337+P317, P362+P364, P391, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 1915 reports by companies from 16 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
危険有害性情報
Regulatory Information
Chemical: 10-Undecenoic acid
Chemical: Undecenoic acid
10-Undecenoic acid is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 10-Undecenoic acid are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)
REACH registered substance: Undec-10-enoic acid (EC: 203-965-8)
Undecylenic acid: HSNO Approval: HSR003810 Approved with controls
Other Safety Information
IMAP assessments - 10-Undecenoic acid: Human health tier I assessment
Evaluation - Chemicals that are unlikely to require further regulation to manage risks to environment
Hazards Summary
Safe when used as a flavoring agent in food; [JECFA] A severe skin irritant; Causes somnolence, excitement, and muscle contraction or spasticity in oral lethal-dose studies of mice; Causes other changes in blood in 3-day intermittent dermal study of mice (15,000 mg/kg); [RTECS] A skin and strong eye irritant; [Alfa Aesar MSDS]
EPA Safer ChemicalChemical: Undecylenic acid
Hazard Classes and CategoriesSkin Irrit. 2 (100%)
化学と産業
薬理情報
ATC Code
D - Dermatologicals
QD - Dermatologicals
Protein BindingNo information regarding protein binding.
Pharmacodynamics
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.
Mechanism of Action
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.
Biological Half-LifeNo information regarding half-life.
Metabolism/MetabolitesNo information regarding metabolism.
Absorption, Distribution and Excretion
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.
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