Phytomonic acid
Basic information
- CAS
503-06-0- Standard SMILES
CCCCCCC1CC1CCCCCCCCCC(=O)O- InChIKey
IJKRDVKGCQRKBI-UHFFFAOYSA-N- Molecular formula
- C19H36O2
- Average molar mass
- 296.5 g/mol
- Monoisotopic mass
- 296.27153039
Overview
11,12-methyleneoctadecanoic acid is a C18, saturated fatty acid composed of octadecanoic acid having an 11,12-methylene substituent forming a cyclopropane. It is a long-chain fatty acid, a saturated fatty acid and a carbocyclic fatty acid.
Names & identifiers
- Preferred name
- Phytomonic acid
- IUPAC
- 10-(2-hexylcyclopropyl)decanoic acid
- English name
- phytomonic acid
- Molecular formula
- C19H36O2
- Molecular weight
- 296.49
Names & synonyms
Phytomonic acidRefChem:929242503-06-010-(2-Hexylcyclopropyl)decanoic acid11,12-methyleneoctadecanoic acidSCHEMBL524999orb2283723CHEBI:61456DTXSID10964568IJKRDVKGCQRKBI-UHFFFAOYSA-NCyclopropanedecanoic acid, 2-hexyl-10-(2-Hexylcyclopropyl)decanoic acid #
Show more names
Decanoic acid, 10-(2-hexylcyclopropyl)HY-124003CS-0083841T84507Q27131091
Database identifiers
- CAS
503-06-0- PubChem CID
- 10417
- DTXSID
DTXSID10964568- ChEBI
CHEBI:61456- Nikkaji
- J503.373J
Properties
Computed structural properties
- XLogP
- 7.2
- Topological polar surface area
- 37.3 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 2
- Rotatable bonds
- 15
- Heavy atoms
- 21
- Formal charge
- 0
- Complexity
- 262
Physicochemical properties
- Melting point
- 24 °C · 24 °C
- Boiling point
- 408.7 · 408.7±13.0 °C(Predicted)
- Density
- 0.923 · 0.923±0.06 g/cm3(Predicted)
- solubility
- 20 mg/ml; · DMF: 20 mg/ml; DMSO: 20 mg/ml; Ethanol: 35 mg/ml; Ethanol:PBS 1:1: 0.5 mg/ml; Water: 0.5 mg/ml
- form
- A solid
- pka
- 4.78 · 4.78±0.10(Predicted)
- FDA UNII
- 8 S87RL · SVS08S87RL
Chemistry & industry
Applications
DescriptionPhytomonic acid is a saturated fatty acid found mainly in a gram-negative bacteria, L. arabinosus, but also in protozoa and in the seed oil of B. coccineus (Connaraceae). Its cyclopropane ring structure has some properties of a double bond, and it may serve to regulate cell membrane fluidity.
UsesPhytomonic acid is a long-chain fatty acid containing a cyclopropane ring produced by Lactobacillus reuteri. Lactobacilli that normally produce Lactobacillic acid also have the ability to resist TNF-α[1].
Additional notes
DefinitionChEBI: An 11,12-methyleneoctadecanoic acid having (11R,12S)-configuration.
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