基本情報
- CAS
141-24-2- 標準SMILES
CCCCCC[C@@H](O)C/C=C\CCCCCCCC(=O)OC- InChIKey
XKGDWZQXVZSXAO-ADYSOMBNSA-N- 分子式
- C19H36O3
- 平均分子量
- 312.5 g/mol
- 単同位体質量
- 312.26644501
名称と識別子
- 優先名称
- Methyl Ricinoleate
- IUPAC
- methyl (Z,12R)-12-hydroxyoctadec-9-enoate
- 現地名
- リシノール酸メチル
- 英語名
- METHYL RICINOLEATE
- 分子式
- C19H36O3
- 分子量
- 312.49
名称と別名
名称をさらに表示
データベース識別子
- CAS
141-24-2、23224-20-6- PubChem CID
- 5354133
- DTXSID
DTXSID2029169- ChEMBL
CHEMBL3183150- ChEBI
CHEBI:156194- UNII
- 90FDR3O96Y
- EC Number
- 205-472-3
- Nikkaji
- J25.083J
物性
構造計算による物性
- XLogP
- 6.1
- 極性表面積
- 46.5 Ų
- 水素結合供与体数
- 1
- 水素結合受容体数
- 3
- 回転可能結合数
- 16
- 重原子数
- 22
- 形式電荷
- 0
- 複雑度
- 274
実験および物理化学的性質
Physical Description
Liquid
Colorless liquid; [HSDB]
物理化学的性質
- 融点
- -29 °C · -29°C
- 沸点
- 170 °C · 170°C 1mm
- 比重(密度)
- 0 · 0,925 g/cm3
- Pour Point
- -29 · -29
- 蒸気圧
- 0.091 Pa · 0.091Pa at 20℃
- 屈折率
- 1.4638 · 1.4638 (589.3 nm 16℃)
- 闪点
- 209 °C · 209 °C
- 貯蔵温度
- -20 °C · Keep in dark place,Inert atmosphere,Store in freezer, under -20°C
- 溶解性
- 50 mg/ml; · DMF: 50 mg/ml; DMSO: 50 mg/ml; Ethanol: 100 mg/ml; Ethanol:PBS (pH 7.2) (1:1): 0.5 mg/ml
- 外見
- 液体
- 酸解離定数(Pka)
- 15.1 · 15.10±0.20(Predicted)
- 臭い (Odor)
- Virtually odourless when pure but usually carries a faint, not unpleasant, oily-fatty, mild and bland odour.
- BRN
- 6132055 · 6132055
- Henry's Law Constant
- 6.7 · 6.7×101 mol/(m3Pa) at 25℃, HSDB (2015)
- 安定性
- Light Sensitive
- 化粧品成分の機能
- 皮膚コンディショニング剤 - 保湿剤スキンコンディショニング
- InChI
- 1S/C19H36O3/c1-3-4-5-12-15-18(20)16-13-10-8-6-7-9-11-14-17-19(21)22-2/h10,13,18,20H,3-9,11-12,14-17H2,1-2H3/b13-10-/t18-/m1/s1
- InChIKey
- XKGDWZQXVZSXAO-ADYSOMBNSA-N
- SMILES
- O=C(OC)CCCCCCC/C=C\C[C@H](O)CCCCCC
- LogP
- 5.1 at · 5.1 at 25℃
- CAS データベース
- 141 · 141-24-2
- EPAの化学物質情報
- Methyl ricinoleate (141-24-2)
安全と法規制
GHS分類
GHS Classification
This chemical does not meet GHS hazard criteria for 100% (141 of 141) of all reports.
Not Classified;Reported as not meeting GHS hazard criteria by 141 of 141 companies. For more detailed information, please visit ECHA C&L website.
Aggregated GHS information provided per 141 reports by companies from 1 notifications to the ECHA C&L Inventory.;Reported as not meeting GHS hazard criteria per 141 of 141 reports by companies.;There are 0 notifications provided by 0 of 141 reports by companies with hazard statement code(s).;Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.
危険有害性情報
Regulatory Information
Chemical: 9-Octadecenoic acid, 12-hydroxy-, methyl ester, (9Z,12R)-
Chemical: 9-Octadecenoic acid, 12-hydroxy-, methyl ester
9-Octadecenoic acid, 12-hydroxy-, methyl ester, (9Z,12R)- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 9-Octadecenoic acid, 12-hydroxy-, methyl ester, (9Z,12R)- 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)
Status: Active Update: 23-05-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/24790;Status: Active Update: 19-04-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/19358
9-Octadecenoic acid, 12-hydroxy-, methyl ester, (9Z,12R)-: Does not have an individual approval but may be used under an appropriate group standard
Other Safety Information
Evaluation - Chemicals that are unlikely to require further regulation to manage risks to human health
Evaluation - Chemicals that are unlikely to require further regulation to manage risks to environment;Evaluation - Chemicals that are unlikely to require further regulation to manage risks to human health
安全と保護具
Disposal Methods
SRP: Criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.
毒性情報
Environmental Fate
TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 3,700(SRC), determined from a structure estimation method(2), indicates that ricinoleic acid, methyl ester is expected to have slight mobility in soil(SRC). Volatilization of ricinoleic acid, methyl ester from moist soil surfaces may occur(SRC) given an estimated Henry's Law constant of 1.47X10-7 atm-cu m/mole(SRC), using a fragment constant estimation method(3). However, adsorption to soil is expected to attenuate volatilization(SRC). Ricinoleic acid, methyl ester is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 6.85X10-8 mm Hg at 25 °C(SRC), determined from a fragment constant method(4). Biodegradation data in soil were not available(SRC, 2010).
AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 3,700(SRC), determined from a structure estimation method(2), indicates that ricinoleic acid, methyl ester is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces may be expected(3) based upon an estimated Henry's Law constant of 1.47X10-7 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 10 months and 9 years, respectively(SRC). However, volatilization from water surfaces is expected to be attenuated by adsorption to suspended solids and sediment in the water column. The estimated volatilization half-life from a model pond is 175 years if adsorption is considered(5). According to a classification scheme(6), an estimated BCF of 370(SRC), from an estimated log Kow of 6.48(7) and a regression-derived equation(2), suggests the potential for bioconcentration in aquatic organisms is high, provided the compound is not metabolized by the organism(SRC). Biodegradation data in water were not available(SRC, 2010).
ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), ricinoleic acid, methyl ester, which has an estimated vapor pressure of 6.85X10-8 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), is expected to exist solely in the particulate phase in the ambient atmosphere. Particulate-phase ricinoleic acid, methyl ester may be removed from the air by wet or dry deposition(SRC). Ricinoleic acid, methyl ester does not contain chromophores that absorb at wavelengths >290 nm(3), and therefore is not expected to be susceptible to direct photolysis by sunlight(SRC).
Soil Adsorption/Mobility
Using a structure estimation method based on molecular connectivity indices(1), the Koc of ricinoleic acid, methyl ester can be estimated to be 3700(SRC). According to a classification scheme(2), this estimated Koc value suggests that ricinoleic acid, methyl ester is expected to have slight mobility in soil.
Environmental Biodegradation
PURE CULTURE: The average growth of the fungus Aspergillus versicolor and the bacterium Pseudomonas acruginosa on the commercial plasticizer ricinoleic acid, methyl ester, serving as the only carbon source, was 414 and 66 mg, respectively, after incubation for 7 days at 30 °C; flasks contained 2.1 g of ricinoleic acid, methyl ester and 70 mL mineral salts and yeast extract solution(1).
Environmental Bioconcentration
An estimated BCF of 370 was calculated in fish for ricinoleic acid, methyl ester(SRC), using an estimated log Kow of 6.48(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is high(SRC), provided the compound is not metabolized by the organism(SRC).
Volatilization from Water/Soil
The Henry's Law constant for ricinoleic acid, methyl ester is estimated as 1.47X10-7 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that ricinoleic acid, methyl ester may volatilize from water surfaces(2). Based on this Henry's Law constant, the volatilization half-life from a model river (1 m deep, flowing 1 m/sec, wind velocity of 3 m/sec)(2) is estimated as 10 months(SRC). The volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec)(2) is estimated as 9 years(SRC). Ricinoleic acid, methyl ester's Henry's Law constant indicates that volatilization from moist soil surfaces may occur(SRC). However, volatilization from water surfaces is expected to be attenuated by adsorption to suspended solids and sediment in the water column. The estimated volatilization half-life from a model pond is 175 years if adsorption is considered(3). Ricinoleic acid, methyl ester is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 6.85X10-8 mm Hg(SRC), determined from a fragment constant method(4).
Non-Human Toxicity Excerpts
/LABORATORY ANIMALS: Neurotoxicity/ Methyl ricinoleate failed to depress the smooth muscle twitch response over this range /1.25X10+5 to 4X10-4 M/ of test concentrations. Similar results were reported for spontaneously contracting rabbit jejunum.
Environmental Abiotic Degradation
A base-catalyzed second-order hydrolysis rate constant of 3.02X10-2 L/mole-sec(SRC) was estimated using a structure estimation method(1); this corresponds to half-lives of 7.3 years and 270 days at pH values of 7 and 8, respectively(1). Ricinoleic acid, methyl ester does not contain chromophores that absorb at wavelengths >290 nm(2), and therefore is not expected to be susceptible to direct photolysis by sunlight(SRC).
Probable Routes of Human Exposure
According to the 2006 TSCA Inventory Update Report, the number of persons reasonably likely to be exposed in the industrial manufacturing, processing, and use of ricinoleic acid, methyl ester is 1 to 99; the data may be greatly underestimated(1).
NIOSH (NOES Survey 1981-1983) has statistically estimated that 1,509 workers (17 of these were female) were potentially exposed to ricinoleic acid, methyl ester in the US(1). Occupational exposure to ricinoleic acid, methyl ester may occur through inhalation and dermal contact with this compound at workplaces where ricinoleic acid, methyl ester is produced or used. Use data indicate that the general population may be exposed to ricinoleic acid, methyl ester via dermal contact with this compound in consumer products containing ricinoleic acid, methyl ester(SRC).
Environmental Fate/Exposure Summary
Ricinoleic acid, methyl ester's production and use as an emollient in cosmetics and as a plasticizer, lubricant, cutting oil additive, and wetting agent may result in its release to the environment through various waste streams. If released to air, an estimated vapor pressure of 6.85X10-8 mm Hg at 25 °C indicates ricinoleic acid, methyl ester will exist solely in the particulate phase in the atmosphere. Particulate-phase ricinoleic acid, methyl ester will be removed from the atmosphere by wet or dry deposition. Ricinoleic acid, methyl ester does not contain chromophores that absorb at wavelengths >290 nm, and therefore is not expected to be susceptible to direct photolysis by sunlight. If released to soil, ricinoleic acid, methyl ester is expected to have slight mobility based upon an estimated Koc of 3,700. Volatilization from moist soil surfaces may be an important fate process based upon an estimated Henry's Law constant of 1.47X10-7 atm-cu m/mole. However, adsorption to soil is expected to attenuate volatilization. If released into water, ricinoleic acid, methyl ester is expected to adsorb to suspended solids and sediment based upon the estimated Koc. Biodegradation data were not available. Volatilization from water surfaces may occur based upon this compound's estimated Henry's Law constant. Estimated volatilization half-lives for a model river and model lake are 10 months and 9 years, respectively. However, volatilization from water surfaces is expected to be attenuated by adsorption to suspended solids and sediment in the water column. The estimated volatilization half-life from a model pond is 175 years if adsorption is considered. An estimated BCF of 370 suggests the potential for bioconcentration in aquatic organisms is high, provided the compound is not metabolized by the organism. An estimated base-catalyzed second-order hydrolysis rate constant of 3.02X10-2 L/mole-sec corresponds to half-lives of 7.3 years and 270 days at pH values of 7 and 8, respectiv
法規制情報
Regulatory Information
Chemical: 9-Octadecenoic acid, 12-hydroxy-, methyl ester, (9Z,12R)-
Chemical: 9-Octadecenoic acid, 12-hydroxy-, methyl ester
9-Octadecenoic acid, 12-hydroxy-, methyl ester, (9Z,12R)- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 9-Octadecenoic acid, 12-hydroxy-, methyl ester, (9Z,12R)- 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)
Status: Active Update: 23-05-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/24790;Status: Active Update: 19-04-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/19358
9-Octadecenoic acid, 12-hydroxy-, methyl ester, (9Z,12R)-: Does not have an individual approval but may be used under an appropriate group standard
安全データ
- F
- 8-10-21
- wgk
- 3
- tsca
- TSCA listed
- hs_code
- 2918195000
- 化審法
- (2)-1332, (2)-1341
- 消防法
- 危-4-4-III
- ストレージクラス
- 10 - Combustible liquids
- 有毒物質データの
- 141-24-2(Hazardous Substances Data)
化学と産業
薬理情報
用途と製造
Uses
CIR ingredient: Methyl Ricinoleate
Used as a cutting oil additive, wetting agent, plasticizer (cellulose acetate butyrate resins, cellulose nitrate resins, ethyl cellulose resins, and polyvinyl acetate and butyral resins), lubricant for phenolic molding compounds, cosmetic additive for lipsticks, and intermediate for nylon 11; [HSDB]
Metal Machining [Category: Heat or Machine];Plastic Composites Manufacturing [Category: Industry]
Noncosmetic uses of methyl ricinoleate include: plasticizer, lubricant, cutting oil additive, and wetting agent.
Used as a skin conditioning agent (emollient)
PLASTICIZER FOR CELLULOSE ACETATE BUTYRATE RESINS
U.S. Exports
(1979) No Data
(1981) No Data
U.S. Imports
(1979) No Data
(1981) No Data
U.S. Production
2023: <75,000 lb;2022: 75,000 - <500,000 lb;2021: 75,000 - <500,000 lb;2020: 500,000 - <1,000,000 lb
(1979) PROBABLY GREATER THAN 2.27X10+6 GRAMS
(1981) PROBABLY GREATER THAN 2.27X10+6 GRAMS
9-Octadecenoic acid, 12-hydroxy-, methyl ester, (9Z,12R)- is listed as a High Production Volume (HPV) chemical (65FR81686). Chemicals listed as HPV were produced in or imported into the U.S. in >1 million pounds in 1990 and/or 1994. The HPV list is based on the 1990 Inventory Update Rule. (IUR) (40 CFR part 710 subpart B; 51FR21438).
9-Octadecenoic acid, 12-hydroxy-, methyl ester, (9Z,12R)- is listed as an Extended High Production Volume (EHPV). Chemicals listed as EHPV were produced in or imported into the U.S. in >1 million pounds according to the 2002 Toxic Substances Control Act (TSCA) Inventory Update. The EHPV program is a voluntary initiative that allows companies to demonstrate that adequate screening data exist for organic HPV chemicals.
For more U.S. Production (Complete) data for Ricinoleic acid, methyl ester (6 total), please visit the HSDB record page.
Methods of Manufacturing
Methyl ricinoleate has been obtained by alcoholysis of castor oil, followed by fractional distillation of the crude esters and further purification by low temperature crystallization. According to a more recent source, methyl ricinoleate is a product of either the esterification of ricinoleic acid or the alcoholysis of castor oil; the product is purified by vacuum distillation.
Transesterification of castor oil with excess methyl alcohol followed by vacuum distillation
General Manufacturing Information
All Other Basic Organic Chemical Manufacturing
9-Octadecenoic acid, 12-hydroxy-, methyl ester, (9Z,12R)-: ACTIVE
Methyl ricinoleate is among the substances that are permitted for use in the formulation of defoaming agents that have been declared safe for use in the manufacture of paper and paperboard intended for use in packaging, transporting, or holding food.
Polymeric esters of polyhydric alcohols and polycarboxylic acids prepared from glycerin and phthalic anhydride and modified with castor oil are permitted for use in adhesives that have been declared safe for use as components of articles intended for use in packaging, transporting, or holding food. Methyl ricinoleate is also permitted for use in these adhesives.
応用分野
用途有機合成原料。
使用Ricinoleic acid, formally called 12-hydroxy-9-cis-octadecenoic acid is a fatty acid. It is an unsaturated omega-9 fatty acid and a hydroxy acid. It is a major component of the seed oil obtained from mature Castor plant (Ricinus communis L., Euphorbiaceae) seeds or in sclerotium of ergot (Claviceps purpurea Tul., Clavicipitaceae). About 90% of the fatty acid content in castor oil is the triglyceride formed from ricinoleic acid.
上流・下流製品情報
下流製品
サプライヤー100 社
補足説明
定義本品は、ヒマシ油(*)から得られる脂肪酸のメチルエステルであり、次の化学式で表される。参照表示名称:ヒマシ油
関連反応
化合物ノート
読み込み中…