9,12-octadecadienoic acid, methyl ester

9,12-octadecadienoic acid, methyl ester
Compound Structure:
Synonyms: METHYL LINOLENATE;301-00-8;Linolenic acid, methyl ester;Methyl alpha-linolenate;Linolenic acid methyl ester;methyl (9Z,12Z,15Z)-octadeca-9,12,15-trienoate;Methyl all-cis-9,12,15-octadecatrienoate;alpha-Linolenic acid methyl ester
Compound ID: NMPC-515
PubChem ID:

5319706

Molecular Formula: C19H32O2
Canonical SMILES: CCC=CCC=CCC=CCCCCCCCC(=O)OC
InChIKey: DVWSXZIHSUZZKJ-YSTUJMKBSA-N
About the compound:

Methyl linolenate, with the molecular formula C19H32O2, is a polyunsaturated fatty acid ester derived from alpha-linolenic acid. This compound is primarily used in scientific studies related to the oxidation and peroxidation of unsaturated fatty acids. Its properties make it a subject of interest in research concerning the prevention of these chemical processes. Moreover, methyl linolenate has been explored for potential applications in dermatology, specifically as a skin whitening agent with anti-melanogenesis activity[1,2]. The chemical exhibits a melting point of -57°C and a boiling point of 182°C at 3 mmHg. It is stored at temperatures between 2-8°C to maintain stability and prevent degradation. The compound is typically handled in liquid form and has a refractive index of n20/D 1.470. These physicochemical properties are crucial for its handling and application in various research settings [3,4].

References 

1. National Institute of Standards and Technology. (n.d.). 9,12,15-Octadecatrienoic acid, methyl ester, (Z,Z,Z)-. Retrieved from https://webbook.nist.gov

2. ChemicalBook. (n.d.). Methyl Linolenate. Retrieved from https://www.chemicalbook.com/ProductChemicalPropertiesCB62304320_EN.htm

3. Sigma-Aldrich. (n.d.). Methyl linolenate = 99% GC. Retrieved from https://www.sigmaaldrich.com

4. Local Pharma Guide. (n.d.). Methyl Linolenate | CAS NO. 301-00-8 | C19H32O2. Retrieved from https://www.localpharmaguide.com/chemicalDetails.php?id=173083

GHS Hazard Statements

H317 (100%): May cause an allergic skin reaction [Warning Sensitization, Skin]

H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]

H400 (100%): Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard]

H410 (100%): Very toxic to aquatic life with long lasting effects [Warning Hazardous to the aquatic environment, long-term hazard]


Properties:

Chemical and Physical Properties

Property Name

Property Value

Molecular Weight

292.5 g/mol

XLogP3-AA

6.2

Hydrogen Bond Donor Count

0

Hydrogen Bond Acceptor Count

2

Rotatable Bond Count

14

Exact Mass

292.240230259 g/mol

Monoisotopic Mass

292.240230259 g/mol

Topological Polar Surface Area

26.3²

Heavy Atom Count

21

Formal Charge

0

Complexity

314

Isotope Atom Count

0

Defined Atom Stereocenter Count

0

Undefined Atom Stereocenter Count

0

Defined Bond Stereocenter Count

3

Undefined Bond Stereocenter Count

0

Covalently-Bonded Unit Count

1

Compound Is Canonicalized

Yes

Physical Description

colourless to pale yellow liquid

Density

0.883-0.893 (20°)

Source: PubChem

Source Species: Crateva adansonii
Eichhornia crassipes
Hibiscus asper
Nymphaea lotus
Phyllanthus amarus
Plumbago zeylanica
Spondias mombin
Azanza garckeana
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