octadeca-9,12-dienoic acid

• ChemBase ID: 102244
• Molecular Formular: C18H32O2
• Molecular Mass: 280.44548
• Monoisotopic Mass: 280.24023026
• SMILES: CCCCC/C=C/C/C=C/CCCCCCCC(=O)O
• Canonical SMILES: CCCCC/C=C/C/C=C/CCCCCCCC(=O)O
• InChI: InChI=1S/C18H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h6-7,9-10H,2-5,8,11-17H2,1H3,(H,19,20)
• InChIKey: OYHQOLUKZRVURQ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: octadeca-9,12-dienoic acid; (9E,12E)-octadeca-9,12-dienoic acid
• IUPAC Traditional name: 9,12-octadecadienoic acid; linoelaidic acid
• Synonyms: trans-9,trans-12-Octadecadiensäure; Linolelaidic acid; cis-9-cis-12-Octadecadienoic acid; LINOLEIC ACID; 9,12-Octadecadienoic Acid; Leinoleic Acid; 9,12-Linoleic Acid; LINOLEIC ACID FREE ACID; trans-9,trans-12-Octadecadienoic acid; LINOELAIDIC ACID; trans ; trans-9,12-octadecadienoic acid; (9E,12E)-octadeca-9,12-dienoic acid; trans-9,trans-12-Octadecadienoic acid solution; Linoelaidic acid solution; Linolelaidic acid solution; 9-cis,12-cis-Linoleic acid; Telfairic acid; cis-9,cis-12-Octadecadienoic acid; Linoleic acid; 反-9,反-12-十八碳二烯酸; 反亚油酸; 反亚油酸 溶液; 顺-9,顺-12-十八碳二烯酸; 亚油酸

Database IDs

• CAS Number: 60-33-3; 506-21-8
• EC Number: 200-470-9
• MDL Number: MFCD00004435; MFCD00064241
• Beilstein Number: 2210856; 1727101
• PubChem SID: 24882204; 24896270; 162088642; 24901678; 24896275; 24896279; 24882205
• PubChem CID: 5282457
• CHEMBL: 93204
• Chemspider ID: 4445609
• FEMA ID: 3380
• Wikipedia Title: Linoelaidic_acid
• Council of Europe Number: 694
• Flavis Number: 8.041

CALCULATED PROPERTIES

• Acid pKa: 4.9881673
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 5.7939434
• LogD (pH = 7.4): 4.040287
• Log P: 6.421877
• Molar Refractivity: 88.5188 cm^3
• Polarizability: 33.928547 Å^3
• Polar Surface Area: 37.3 Å^2
• Rotatable Bonds: 14
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: ethanol: soluble; NaOH: soluble1 M
• Apperance: liquid
• Melting Point: -5 °C (23 °F); -12 °C (10 °F); -5 °C; -5 °C(lit.)
• Boiling Point: 229-230 °C (444-446 °F); 229-230 °C at 16 mmHg; 229-230 °C/16 mmHg(lit.)
• Flash Point: >113 °C; >235.4 °F; 14 °C; 57.2 °F
• Density: 0.89 g/ml; 0.89 g/mL at 25 °C(lit.); 0.902 g/mL at 25 °C(lit.); 0.9022 (water = 1)
• Refractive Index: n20/D 1.466; n20/D 1.466(lit.); n20/D 1.469; n20/D 1.470
• Vapor Pressure: Very low at 25 °C, 16 mm Hg (2.13 kPa) at 229 °C

Safety Information

• Storage Condition: 0°C; 0°C, Store Under Nitrogen
• RTECS: RF9990000
• European Hazard Symbols: Flammable (F)
• German water hazard class: 1; 3
• Risk Statements: 11
• Safety Statements: 16
• GHS Pictograms: GHS02
• GHS Signal Word: Danger
• GHS Hazard statements: H225
• GHS Precautionary statements: P210
• Personal Protective Equipment: Eyeshields, Gloves; Eyeshields, Gloves, half-mask respirator (US), multi-purpose combination respirator cartridge (US)
• Storage Temperature: -20°C; 2-8°C

Pharmacology Properties

• Gene Information: human ... SOAT1(6646), SOAT2(8435)
• Allergens: no known allergens

Product Information

• Purity: ~60%; ~65%; ≥85% (GC); ≥93% (GC); ≥98.0% (GC); ≥98.0% (HPLC); ≥98.5% (GC); ≥99%; 60-74% (GC); 95-99%; 99%
• Concentration: ~250 mg/mL in ethanol
• Grade: analytical standard; NI; technical
• Suitability: suitable for cell culture
• Impurities: 18-32% oleic acid
• Shelf Life: (limited shelf life, expiry date on the label)
• Quality: natural
• Product Line: BioReagent
• Linear Formula: CH3(CH2)4CH=CHCH2CH=CH(CH2)7CO2H
• Empirical Formula (Hill Notation): C18H32O2
• Classification: Derivatives & analogs of Natural Compounds

DETAILS

MP Biomedicals - 02194695

Cell Culture Reagent
Free Acid
Purity: 95-99%

MP Biomedicals - 02155239

(trans-9,trans-12-Octadecadienoic acid) Purity: 99% Sealed ampule(liquid). 1 ml = approx. 0.89 g

MP Biomedicals - 02100805

Free Acid
Purity: 95-99%

MP Biomedicals - 02102187

Free Acid
Purity: ~65%
1 ml = approx. 0.90 g

Sigma Aldrich - L1626

Biochem/physiol Actions
Linoleic acid increases cell proliferation and gene expression of PPARα and its target genes such as acyl-CoA oxidase in primary duck hepatocytes 1.

Sigma Aldrich - L1268

Biochem/physiol Actions
Linoleic acid increases cell proliferation and gene expression of PPARα and its target genes such as acyl-CoA oxidase in primary duck hepatocytes 1.

Sigma Aldrich - L1376

Packaging
1, 5, 10, 25 g in ampule
500 mg in ampule
10 mg in autosmp vl
Biochem/physiol Actions
Linoleic acid increases cell proliferation and gene expression of PPARα and its target genes such as acyl-CoA oxidase in primary duck hepatocytes 1.
Linoleic acid is an n-6 polyunsaturated essential fatty acid (PUFA) used as a precursor of arachidonic acid (AA) and various prostaglandins. Linoleic acid may be used to improve the delivery and efficacy of anticancer drugs and in cancer protection.

Sigma Aldrich - L1012

Application
Fatty acid that is typically bound to a carrier molecule such as BSA or cyclodextrin for use in cell culture.
Packaging
Sealed ampule.
Biochem/physiol Actions
Linoleic acid increases cell proliferation and gene expression of PPARα and its target genes such as acyl-CoA oxidase in primary duck hepatocytes 1.

Sigma Aldrich - W338001

Packaging
1 kg in glass bottle
1 sample in glass bottle
25, 100 g in glass bottle
Biochem/physiol Actions
Linoleic acid increases cell proliferation and gene expression of PPARα and its target genes such as acyl-CoA oxidase in primary duck hepatocytes 1.

Sigma Aldrich - 233927

Biochem/physiol Actions
Linoleic acid increases cell proliferation and gene expression of PPARα and its target genes such as acyl-CoA oxidase in primary duck hepatocytes 1.

Sigma Aldrich - 62240

Caution
partially crystallizes on storage at 0-4°C
Packaging
1 L in glass bottle
250 mL in glass bottle
Biochem/physiol Actions
Linoleic acid increases cell proliferation and gene expression of PPARα and its target genes such as acyl-CoA oxidase in primary duck hepatocytes 1.

Sigma Aldrich - 62230

Biochem/physiol Actions
Linoleic acid increases cell proliferation and gene expression of PPARα and its target genes such as acyl-CoA oxidase in primary duck hepatocytes 1.

Sigma Aldrich - 62235

Biochem/physiol Actions
Linoleic acid increases cell proliferation and gene expression of PPARα and its target genes such as acyl-CoA oxidase in primary duck hepatocytes 1.