(9Z)-octadec-9-enoic acid

• ChemBase ID: 128715
• Molecular Formular: C18H34O2
• Molecular Mass: 282.46136
• Monoisotopic Mass: 282.25588033
• SMILES: CCCCCCCC/C=C\CCCCCCCC(=O)O
• Canonical SMILES: CCCCCCCC/C=C\CCCCCCCC(=O)O
• InChI: InChI=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-
• InChIKey: ZQPPMHVWECSIRJ-KTKRTIGZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (9Z)-octadec-9-enoic acid
• IUPAC Traditional name: oleic acid
• Synonyms: (9Z)-9-Octadecenoic Acid; cis-9-Octadecenoic Acid; (9Z)-Octadecenoic acid; (Z)-Octadec-9-enoic acid; cis-9-Octadecenoic acid; cis-Δ^9-Octadecenoic acid; Oleic acid; 18:1 cis-9; Oleic acid; Oleic acid; Oleic Acid–Cyclodextrin Complex; Oleic Acid-Water Soluble; 十八烯酸; 顺式-9-十八烯酸; 油酸

Database IDs

• CAS Number: 112-80-1
• EC Number: 204-007-1
• MDL Number: MFCD00064242
• Beilstein Number: 1726542
• Merck Index: 146828
• PubChem SID: 24897936; 24897946; 24278605; 162223021
• PubChem CID: 445639
• CHEMBL: 8659
• Wikipedia Title: Oleic_acid

CALCULATED PROPERTIES

• Acid pKa: 4.9881673
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 6.155865
• LogD (pH = 7.4): 4.4022083
• Log P: 6.783798
• Molar Refractivity: 87.4022 cm^3
• Polarizability: 34.16541 Å^3
• Polar Surface Area: 37.3 Å^2
• Rotatable Bonds: 15
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: H2O: soluble50 mg/mL, clear to slightly hazy; Insoluble in water; Soluble in methanol
• Apperance: Liquid; Pale yellow or brownish yellow oily liquid with lard-like odor; powder
• Melting Point: 13 - 14°C; 13-14 °C(lit.); 13-14°C
• Boiling Point: 194-195 °C/1.2 mmHg(lit.); 286°C/100mm; 360°C
• Flash Point: 113 °C; 235.4 °F
• Density: 0.887; 0.89 g/mL at 25 °C(lit.); 0.895 g/mL
• Refractive Index: 1.4610; n20/D 1.459(lit.)
• Vapor Pressure: 1 mmHg ( 176 °C)

Safety Information

• Storage Condition: Refrigerator
• Storage Warning: Air Sensitive
• RTECS: RG2275000
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 1; 3
• Risk Statements: 36/37/38; 36/38; 38
• Safety Statements: 26-36; 26-37; 36/37/39
• TSCA Listed: 是
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• NFPA704:
  

  1

  0

  0
• GHS Hazard statements: H315; H315-H319; H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338; P280-P305+P351+P338-P302+P352-P321-P362-P332+P313
• Personal Protective Equipment: Eyeshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• Storage Temperature: -20°C

Pharmacology Properties

• Gene Information: human ... PRKCA(5578), PRKCB(5579), PRKCD(5580), PRKCE(5581), PRKCG(5582), PRKCH(5583), PRKCI(5584), SOAT1(6646), SOAT2(8435); human ... SOAT1(6646), SOAT2(8435)

Product Information

• Purity: ≥93% (GC); ≥99% (GC); 99%; tech. 90%
• Compostion: Oleic acid, ~30 mg/g (balance methyl-β-cyclodextrin)
• Suitability: suitable for cell culture
• Quality Level: PREMIUM

DETAILS

Sigma Aldrich - O1257

Other Notes
Methyl-β-cylodextran binding improves the solubility and delivery of Oleic acid in culture media.

Sigma Aldrich - O1008

Frequently Asked Questions
Live Chat and Frequently Asked Questions are available for this Product.
Biochem/physiol Actions
氧化磷酸化的解偶联。抑制 2,4-二硝基酚激活的 ATP 酶。加入血清白蛋白可使作用相反。
激活肝细胞中的蛋白激酶 C。
包装
1, 5, 25 g in ampule
密封安瓿瓶包装

Sigma Aldrich - O1630

Biochem/physiol Actions
氧化磷酸化的解偶联。抑制 2,4-二硝基酚激活的 ATP 酶。加入血清白蛋白可使作用相反。
激活肝细胞中的蛋白激酶 C。
包装
Sealed ampule

Toronto Research Chemicals - O524201

Oleic acid is a monounsaturated omega-9 fatty acid. Oleic Acid is obtained by the hydrolysis of various animal and vegetable fats and oils. Oleic Acid is used as an emulsifying or solubilizing agent in aerosol products.

REFERENCES

• Mahsut, A. et al.: Anal. Biochem., 408, 351 (2011)
• Brock, K., et al.: Br. J. Nut., 101, 1228 (2011)
• Soveral, G., et al.: Biochem. Biophys. Res. Comm., 383, 108 (2011)