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油酸

油酸用途

Oleic acid 是人脂肪细胞和其他组织中最常见的单不饱和脂肪酸。

油酸名称

[ CAS 号 ]:
112-80-1

[ 中文名 ]:
油酸

[ 英文名 ]:
oleic acid

[中文别名 ]:

顺式十八碳-9-烯酸

[英文别名 ]:

oleicacidamide-heptaglycolether
Oleic Acid
adogen73
Amide O
OLEAMID
Armid O
Slip-eze
AMD-O
octadec-9-enoic acid
MFCD00003274

油酸生物活性

[ 描述 ]:

Oleic acid 是人脂肪细胞和其他组织中最常见的单不饱和脂肪酸。

[ 相关类别 ]:

天然产物 >> 酸和醛

研究领域 >> 其他

[ 靶点 ]

Human Endogenous Metabolite

[体外研究]

油酸是人脂肪细胞和其他组织中最常见的单不饱和脂肪酸(FA)。油酸通过增强AMPK活化介导的β-氧化促进高转移癌细胞中的细胞增殖和迁移。油酸抑制癌细胞在低转移癌细胞(如胃癌SGC7901和乳腺癌MCF-7细胞系)中的生长和存活[1]。

[参考文献]

[1]. Li S, et al. High metastaticgastric and breast cancer cells consume oleic acid in an AMPK dependent manner. PLoS One. 2014 May 13;9(5):e97330.

[相关活性小分子]

油酸物理化学性质

[ 密度 ]:
0.9±0.1 g/cm3

[ 沸点 ]:
360.0±0.0 °C at 760 mmHg

[ 熔点 ]:
13-14 °C(lit.)

[ 分子式 ]:
C₁₈H₃₄O₂

[ 分子量 ]:
282.461

[ 闪点 ]:
270.1±14.4 °C

[ 精确质量 ]:
282.255890

[ PSA ]:
37.30000

[ LogP ]:
7.70

[ 外观性状 ]:
无色至淡黄色粘性液体

[ 蒸汽密度 ]:
1.03 (vs air)

[ 蒸汽压 ]:
0.0±1.7 mmHg at 25°C

[ 折射率 ]:
1.467

[ 储存条件 ]:
2-8°C

[ 稳定性 ]:
Stable. Combustible. Incompatible with strong oxidizing agents, aluminium.

[ 水溶解性 ]:
negligible

油酸MSDS

油酸毒性和生态

CHEMICAL IDENTIFICATION

RTECS NUMBER :: RG2275000

CHEMICAL NAME :: 9-Octadecenoic acid, (Z)-

CAS REGISTRY NUMBER :: 112-80-1

BEILSTEIN REFERENCE NO. :: 1726542

LAST UPDATED :: 199710

DATA ITEMS CITED :: 17

MOLECULAR FORMULA :: C18-H34-O2

MOLECULAR WEIGHT :: 282.52

WISWESSER LINE NOTATION :: QV8U9 -C

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: Standard Draize test

ROUTE OF EXPOSURE :: Administration onto the skin

SPECIES OBSERVED :: Human

TYPE OF TEST :: Open irritation test

ROUTE OF EXPOSURE :: Administration onto the skin

SPECIES OBSERVED :: Rodent - rabbit

TYPE OF TEST :: Standard Draize test

ROUTE OF EXPOSURE :: Administration into the eye

SPECIES OBSERVED :: Rodent - rabbit

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 74 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 2400 ug/kg

TOXIC EFFECTS :: Lungs, Thorax, or Respiration - acute pulmonary edema Lungs, Thorax, or Respiration - other changes

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 282 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 230 mg/kg

TOXIC EFFECTS :: Behavioral - convulsions or effect on seizure threshold

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - rabbit

DOSE/DURATION :: 390 mg/kg/17W-I

TOXIC EFFECTS :: Tumorigenic - equivocal tumorigenic agent by RTECS criteria Tumorigenic - tumors at site of application

TYPE OF TEST :: Unscheduled DNA synthesis

MUTATION DATA

TYPE OF TEST :: Cytogenetic analysis

TEST SYSTEM :: Rodent - hamster Fibroblast

DOSE/DURATION :: 2500 ug/L

REFERENCE :: CRNGDP Carcinogenesis (London). (Oxford Univ. Press, Pinkhill House, Southfield Road, Eynsham, Oxford OX8 1JJ, UK) V.1- 1980- Volume(issue)/page/year: 3,499,1982 *** U.S. STANDARDS AND REGULATIONS *** EPA FIFRA 1988 PESTICIDE SUBJECT TO REGISTRATION OR RE-REGISTRATION FEREAC Federal Register. (U.S. Government Printing Office, Supt. of Documents, Washington, DC 20402) V.1- 1936- Volume(issue)/page/year: 54,7740,1989 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOHS - National Occupational Hazard Survey (1974) NOHS Hazard Code - 52190 No. of Facilities: 65952 (estimated) No. of Industries: 312 No. of Occupations: 196 No. of Employees: 796897 (estimated) NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - 52190 No. of Facilities: 49332 (estimated) No. of Industries: 256 No. of Occupations: 181 No. of Employees: 1078478 (estimated) No. of Female Employees: 410362 (estimated)

油酸安全信息

[ 符号 ]:

GHS07

[ 信号词 ]:
Warning

[ 危害声明 ]:
H315

[ 个人防护装备 ]:
Eyeshields;full-face respirator (US);Gloves;multi-purpose combination respirator cartridge (US);type ABEK (EN14387) respirator filter

[ 危害码 (欧洲) ]:
Xi:Irritant

[ 风险声明 (欧洲) ]:
R36/37/38

[ 安全声明 (欧洲) ]:
S36/37-S37/39-S26-S36

[ 危险品运输编码 ]:
UN 1198 3/PG 3

[ WGK德国 ]:
2

[ RTECS号 ]:
LP8925000

[ 海关编码 ]:
2916150000

油酸合成路线

油酸上下游产品

油酸上游产品

油酸下游产品

油酸制备

1、油酸与其他脂肪酸一起，以甘油酯的形式存在于一切动植物油脂中。在动物脂肪中，油酸在脂肪酸中约占40-50%。植物油中的含量变化较大，茶油中可高达83%，花生油中达54%，而椰子油中则只有5-6%。油酸为生产硬脂酸时的联产品，工业硬脂酸和工业油酸实际上都含有其他脂肪酸。用于生产硬脂酸和油酸的油脂原料很多，工业上一般取混合油脂配方，例如熔制牛脂30%、熔制猪脂10%、骨脂40%和棉籽油20%。油脂经精制、水解得到的混合脂肪酸中，饱和酸与不饱和酸熔点差异较大。硬脂酸和油酸的收率主要决定于油酯配方，一般情况下，冷榨可以得到30-50%油酸，50-70%硬脂酸。以动植物油脂和乳化液于105℃下水解，用硬脂酸净化，经一次压榨除去硬脂酸，分离得粗油酸，经脱水、蒸馏、冷冻。再经二次压榨，除去软脂酸，最后经脱水精制而得成品。本法可联产硬脂酸，同样由油酸制硬脂酸时，也会联产油酸。原料消耗定额：动植物油脂1950kg/t、硫酸（98%）210kg/t。

2、用含有一定量油酸的油脂为原料，如牛脂、猪油、棕榈油，使分解出脂肪酸，用溶剂使脂肪酸溶解并冷却，除去固体脂肪酸而得粗油酸。再用溶剂溶解，在低温下冷却使油酸结晶而出。

精制方法：在-10~ -60℃用丙酮重结晶，可从亚油酸和饱和脂肪酸中分离出油酸。残留的饱和脂肪酸可在乙醇中生成铅盐而沉淀，然后再蒸馏精制。一般市售油酸可用丙酮在-11℃结晶，将晶体研碎后真空干燥一周即可。其他的精制方法有：将油酸转变为油酸甲酯，分馏后将酯水解，游离酸用丙酮在-40~ -45℃重结晶。每1g油酸用12mL丙酮。也有将油酸的熔融物分步结晶，然后在133.3MPa压力下进行分子蒸馏精制的方法。

3.取油脂水解可得混合脂肪酸，冷榨所得液体部分即为油酸，除去固体部分饱和脂肪酸。可用丙酮作溶剂精制得到纯品。

4.采用硬脂酸联产法。在合成硬脂酸时,把压榨后的不饱和脂肪酸进一步冷冻压榨,分离饱和脂肪酸,再经脱水而得。或在制取植物油时,将皂脚经皂化、酸化、分离、蒸馏而得。.

5. 烟草：OR，44，FC，9， 13， 37， 41， 44；OR，26；FC，BU，OR，18；BU，9；BU，10；FC，BU，OR，19

油酸海关

[ 海关编码 ]: 2916150000

[ 中文概述 ]:
2916150000 油酸、亚油酸或亚麻酸及其盐和酯。监管条件:无。增值税率:17.0%。退税率:9.0%。最惠国关税:6.5%。普通关税:30.0%

[ 申报要素 ]: 品名, 成分含量, 用途, 丙烯酸、丙烯酸盐或酯应报明包装, 碳18/16含量

[ Summary ]:
2916150000 oleic, linoleic or linolenic acids, their salts and esters。Supervision conditions:None。VAT:17.0%。Tax rebate rate:9.0%。MFN tariff:6.5%。General tariff:30.0%

油酸文献

Differential expression of efflux pump genes of Mycobacterium tuberculosis in response to varied subinhibitory concentrations of antituberculosis agents.

Tuberculosis (Edinb.) 95(2) , 155-61, (2015)

Several reports have elaborated on the role of efflux pumps in drug resistance in Mycobacterium tuberculosis by analysing the mRNA expression profiles. However, there is no uniformity in the subinhibi...

Decreased lipogenesis in white adipose tissue contributes to the resistance to high fat diet-induced obesity in phosphatidylethanolamine N-methyltransferase-deficient mice.

Biochim. Biophys. Acta 1851(2) , 152-62, (2015)

Mice lacking phosphatidylethanolamine N-methyltransferase (PEMT, Pemt(-/-) mice) are resistant to high-fat diet (HFD)-induced obesity (DIO) but develop non-alcoholic steatohepatitis. PEMT expression i...

Exploring the impact of drug properties on the extent of intestinal lymphatic transport - in vitro and in vivo studies.

Pharm. Res. 32(5) , 1817-29, (2015)

Intestinal lymphatic transport of specific lipophilic drugs offers therapeutic advantages and maximises oral bioavailability. The aims of this study were; to compare intestinal lymphatic transport of ...

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油酸