ChemFOnt: Showing chemical card for Malvalic acid (CFc000281802)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-14 03:33:33 UTC

Chemfont ID

CFc000281802

Molecule Identification

Common Name

Malvalic acid

Definition

Malvalic acid, also known as 2-octyl-1-cyclopropene-1-heptanoic acid or 8,9-methylen-8-heptadecensaeure, is a member of the class of compounds known as long-chain fatty acids. Long-chain fatty acids are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms. Thus, malvalic acid is considered to be a fatty acid lipid molecule. Malvalic acid is practically insoluble (in water) and a weakly acidic compound (based on its pKa). Malvalic acid can be found in peanut and roselle, which makes malvalic acid a potential biomarker for the consumption of these food products. Malvalic acid is a cyclopropenic fatty acid found in cottonseed oil. The cyclopropene ring is thought to be one of the causes of abnormalities that develop in animals that ingest cottonseed oil. This reactivity could be cause for concern depending on concentration. Hydrogenation of the oil destroys malvalic acid .

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
2-Octyl-1-cyclopropene-1-heptanoic acid	ChEBI
8,9-Methylen-8-heptadecensaeure	ChEBI
8,9-Methylene-8Z-heptadecenoic acid	ChEBI
Malvalsaeure	ChEBI
2-Octyl-1-cyclopropene-1-heptanoate	Generator
8,9-Methylene-8Z-heptadecenoate	Generator
Malvalate	Generator

Chemical Formula

C₁₈H₃₂O₂

Average Molecular Weight

280.4455

Monoisotopic Molecular Weight

280.240230268

IUPAC Name

7-(2-octylcycloprop-1-en-1-yl)heptanoic acid

Traditional Name

malvalic acid

CAS Registry Number

None

SMILES

CCCCCCCCC1=C(CCCCCCC(O)=O)C1

InChI Identifier

InChI=1S/C18H32O2/c1-2-3-4-5-6-9-12-16-15-17(16)13-10-7-8-11-14-18(19)20/h2-15H2,1H3,(H,19,20)

InChI Key

HPSSZFFAYWBIPY-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Long-chain fatty acids

Alternative Parents

Substituents

Long-chain fatty acid
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

long-chain fatty acid (CHEBI:6673 )
monounsaturated fatty acid (CHEBI:6673 )
cyclopropenyl fatty acid (CHEBI:6673 )
Carbocyclic fatty acids (C08321 )
Fatty acids (C08321 )
Carbocyclic fatty acids (LMFA01140002 )

Functional Ontology

Not Available

Exogenous (HMDB: HMDB0302286)

Food

Nut

Peanut (FooDB: FOOD00016)

Herb and spice

Herb

Roselle (FooDB: FOOD00447)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.0036 g/L	ALOGPS
logP	6	ALOGPS
logP	5.92	ChemAxon
logS	-4.9	ALOGPS
pKa (Strongest Acidic)	4.75	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	14	ChemAxon
Refractivity	84.96 m³·mol⁻¹	ChemAxon
Polarizability	36.61 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon