Erucic acid

Erucic acid
Compound Structure:
Synonyms: (Z)-docos-13-enoic acid; (13Z)-13-Docosenoate; (13Z)-13-Docosenoic acid; .delta.13-cis-Docosenoic acid; 13(Z)-Docosenoic Acid; 13-cis-Docosenoic acid; 13-docosenoate; 13-Docosenoic acid; 13-Docosenoic acid, (13Z)-; 13-Docosenoic acid, (Z)
Compound ID: NMPC-1024
PubChem ID:

5281116
Molecular Formula: C22H42O2
Canonical SMILES: CCCCCCCCC=CCCCCCCCCCCCC(=O)O
InChIKey: DPUOLQHDNGRHBS-KTKRTIGZSA-N
About the compound:

Erucic acid is a docosenoic acid having a cis- double bond at C-13. It is found particularly in brassicas - it is a major component of mustard and rapeseed oils and is produced by broccoli, Brussels sprouts, kale, and wallflowers. It is a conjugate acid of an erucate. Erucic Acid is a monounsaturated very long-chain fatty acid with a 22-carbon backbone and a single double bond originating from the 9th position from the methyl end, with the double bond in the cis- configuration. Erucic acid is a monounsaturated omega-9 fatty acid, denoted 22:1ω9. It has the chemical formula :CH3(CH2)7CH=CH(CH2)11CO2H. It is prevalent in wallflower seed and other plants in the family Brassicaceae, with a reported content of 20 to 54% in high erucic acid rapeseed oil[2] and 42% in mustard oil. Erucic acid is also known as cis-13-docosenoic acid and the trans isomer is known as brassidic acid.

GHS Hazard Statements

• H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]

• H319 (97.67%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]

• H335 (93.02%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]
Properties:

Chemical and Physical Properties

Property Name

Property Value

Molecular Weight

338.6 g/mol

XLogP3

8.7

Hydrogen Bond Donor Count

1

Hydrogen Bond Acceptor Count

2

Rotatable Bond Count

19

Exact Mass

338.318480578 g/mol

Monoisotopic Mass

338.318480578 g/mol

Topological Polar Surface Area

37.3Ų

Heavy Atom Count

24

Formal Charge

0

Complexity

284

Isotope Atom Count

0

Defined Atom Stereocenter Count

0

Undefined Atom Stereocenter Count

0

Defined Bond Stereocenter Count

1

Undefined Bond Stereocenter Count

0

Covalently-Bonded Unit Count

1

Compound Is Canonicalized

Yes

Physical Description

Liquid; Other Solid; Pellets or Large Crystals

Boiling Point

265 °C at 15 mm Hg

Melting Point

33.8 °C

Density

0.860 at 55 °C/4 °C

Solubility 

Soluble in ethanol, carbon tetrachloride; very soluble in ethyl ether, methanol

Vapor Pressure

0.00000115 [mmHg]

Source: PubChem                        
Source Species: Urena lobata
Vernonia colorata
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