Oleic Acid 油酸

CAS 112-80-1 MFCD00064242

化学结构图

112-80-1
SMILES: CCCCCCCCC=CCCCCCCCC(=O)O

化学属性

Mol. FormulaC18H34O2
Mol. Weight282.47
Refractive index1.4590 to 1.4630
Boiling Point285°C/100mmHg(lit.)
Density0.89
Melting Point13-14
Vapor Pressure1 mmHg ( 176 °C)
TSCAYes
Flash Point187°C(lit.)
SolubilitySoluble in ethanol (>25 mg/ml), ether, acetone, chloroform, DMF (100 mg/ml), DMSO (100 mg/ml), and PBS (pH 7.2) (<100 μg/ml).
Stability对光线, 空气和热敏感
Appearance liq.

别名和识别编码

Chemical NameOleic Acid
CAS Number112-80-1
Synonym (Z)-9-Octadecenoic acid 9-Octadecenoic acid, (Z)- 9-Octadecensäure, (Z)- cis-9-Octadecenoic acid Acide oleique D 100 D9-cis-octadecenoic acid Edenor ATiO5 Emersol 211 Emersol 214NF Emersol 6313NF Extra Oleic 80R Glycon RO HY-Phi 20 Lunac O-CA Lunac O-P Oleins Pamolyn 100 Tego-oleic 130 Vopcolene 27 Z-9-Octadecenoic acid cis-9-Octadecenoic Acid cis-9-Octadecenoic acid cis-Δ9-Octadecenoic acid octadec-9c-enoic acid Ölsäure, cis Δ9-cis-Oleic acid 油酸
PubChem Substance ID445639
EC Number207-007-1
Beilstein Registry Number1726542
MDL NumberMFCD00064242
Merck Number6828
Chemical Name Translation油酸
Reaxys-RN1726542
Wiswesser Line NotationQV8U9 -C
LabNetwork Molecule IDLN01302976
InChIInChI=1S/C18H34O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h9-10H,2-8,11-17H2,1H3,(H,19,20)/b10-9-
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分类

  • {SNA} Alphabetical Listings, Certified Natural Products, Flavors and Fragrances, Halal Certified Products, Kosher Certified Products, O, O-P, O-Z, 生物活性小分子, 细胞生物学
  • {SNA} Bioactive Small Molecules, Biochemicals and Reagents, Building Blocks, C13 to C42+, Carbonyl Compounds, Carboxylic Acids, Cell Biology, Chemical Synthesis, Core Bioreagents, Fatty Acids and conjugates, Fatty Acyls, Functional Foods, Lipids, Lipids and Related Products, Monoenoic fatty acids,
  • {SNA} Alphabetical Listings,

产品应用

  • An anti-proliferative agent and activator of PKC and CaMKII

相关文献及参考

  • [2]. Jack-Hays MG, et al. Activation of Na+/K(+)-ATPase by fatty acids, acylglycerols, and related amphiphiles: structure-activity relationship. Biochim Biophys Acta. 1996 Feb 21;1279(1):43-8.
  • Mahsut, A. et al.: Anal. Biochem., 408, 351 (2011); Brock, K., et al.: Br. J. Nut., 101, 1228 (2009); Soveral, G., et al.: Biochem. Biophys. Res. Comm., 383, 108 (2009);
  • Merck:14,6828
  • Merck:14,6828 Beilstein: 2,IV,1641
  • Short: II/5
  • Short: III/38A
  • Short: III/38B
  • [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.
  • [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.
  • [2]. Jack-Hays MG, et al. Activation of Na+/K(+)-ATPase by fatty acids, acylglycerols, and related amphiphiles: structure-activity relationship. Bioc

安全信息

GHS Symbol
WGK Germany1
Hazard Codes Xi
Hazard statements
  • H315 Causes skin irritation 会刺激皮肤
  • H319 Causes serious eye irritation 严重刺激眼睛
  • H335 May cause respiratory irritation 可能导致呼吸道刺激
Personal Protective Equipment Eyeshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
RTECSRG2275000
Signal word Warning
Safety Statements
  • S26 In case of contact with eyes, rinse immediately with plenty of water and seek medical advice 眼睛接触后,立即用大量水冲洗并征求医生意见;
  • S36 Wear suitable protective clothing 穿戴适当的防护服;
  • S36/37/39 Wear suitable protective clothing, gloves and eye/face protection 穿戴适当的防护服、手套和眼睛/面保护;
  • S37 Wear suitable gloves 戴适当手套;
  • S37/39 Wear suitable gloves and eye/face protection 穿戴适当的手套和眼睛/面保护;
Risk Statements
  • R36/37/38 Irritating to eyes, respiratory system and skin 对眼睛、呼吸系统和皮肤有刺激性
  • R38 Irritating to skin 刺激皮肤
Precautionary statements
  • P261 Avoid breathing dust/fume/gas/mist/vapours/spray. 避免吸入粉尘/烟/气体/烟雾/蒸汽/喷雾。
  • P264 Wash hands thoroughly after handling. 处理后要彻底洗净双手。
  • P280 Wear protective gloves/protective clothing/eye protection/face protection. 戴防护手套/防护服/眼睛的保护物/面部保护物。
  • P302+P352+P332+P313+P362+P364
  • P305+P351+P338
  • P305+P351+P338+P337+P313
  • P362 Take off contaminated clothing and wash before reuse. 脱掉污染的衣服,清洗后方可重新使用
Storage condition 储存温度-20°C; 充氩保存 0-10°C 密封避光于2-8℃保存 储存温度2-8℃ 储存温度?20°C 密封避光于2-8℃保存,99%储存于-20℃ 储存温度2-8℃,充氩储存 Air Sensitive 0-10
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
REFERENCE :
   CRSBAW Comptes Rendus des Seances de la Societe de Biologie et de Ses
   Filiales.  (SPPIF, B.P.22, F-41353 Vineuil, France)  V.1-    1849-
   Volume(issue)/page/year: 137,760,1943

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
REFERENCE :
   APTOA6 Acta Pharmacologica et Toxicologica.  (Copenhagen, Denmark)  V.1-59,
   1945-86.  For publisher information, see PHTOEH  Volume(issue)/page/year:
   18,141,1961

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
REFERENCE :
   AJPAA4 American Journal of Pathology.  (Lippincott/Harper, Journal
   Fulfillment Dept., 2350 Virginia Ave., Hagerstown, MD 21740)  V.1-    1925-
   Volume(issue)/page/year: 103,376,1981

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
REFERENCE :
   UCDS** Union Carbide Data Sheet.  (Union Carbide Corp., 39 Old Ridgebury
   Rd., Danbury, CT 06817)  Volume(issue)/page/year: 11/29/1963

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
REFERENCE :
   YKKZAJ Yakugaku Zasshi.  Journal of Pharmacy.  (Nippon Yakugakkai, 2-12-15
   Shibuya, Shibuya-ku, Tokyo 150, Japan)  No.1-    1881-
   Volume(issue)/page/year: 104,793,1984

TYPE OF TEST            : Unscheduled DNA synthesis
ROUTE OF EXPOSURE       : Rectal
TEST SYSTEM             : Rodent - mouse
DOSE/DURATION           : 35 mg/kg
REFERENCE :
   CALEDQ Cancer Letters (Shannon, Ireland).  (Elsevier Scientific Pub. Ireland
   Ltd., POB 85, Limerick, Ireland)  V.1-    1975- Volume(issue)/page/year:
   23,253,1984

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

TYPE OF TEST            : Cytogenetic analysis
TEST SYSTEM             : Yeast - Saccharomyces cerevisiae
DOSE/DURATION           : 100 mg/L
REFERENCE :
   NATUAS Nature.  (Nature Subscription Dept., POB 1018, Manasguan, NJ 08736)
   V.1-    1869-  Volume(issue)/page/year: 294,263,1981

其他信息

  • 露置空气中逐渐变成棕色,能溶于醇,苯和氯仿,不溶水。工业品为黄色到红色油状液体,有猪油气味。由于含有双键,在空气中长期放置能发生自氧化,出现腐败的哈喇味。油酸与硝酸作用则异构化为其反式异构体,的反油酸。
  • Oleic Acid, a monounsaturated fatty acid originally derived from Olea europaea, has been shown to be an anti-proliferative agent. This compound has also been reported to promote neuronal differentiation in murine cell cultures. Mechanistic studies suggest that these Oleic Acid effects are mediated by PPARβ. Furthermore, Oleic Acid has demonstrated the ability to stimulate an increase in secretion of collagen I, TGF-β secretion, and extracellular signal-regulated kinase1/2. Oleic Acid is an activator of PKC and CaMKII.

系列性分类


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