Phytomonic acid

Base Information

• Chemical Name: Phytomonic acid
• CAS No.: 503-06-0
• Molecular Formula: C₁₉H₃₆O₂
• Molecular Weight: 296.494
• DSSTox Substance ID: DTXSID10964568
• Nikkaji Number: J503.373J
• Wikidata: Q27131091
• Mol file: 503-06-0.mol

Synonyms:cis-11,12-methyleneoctadecanoic acid;lactobacillic acid;phytomonic acid;phytomonic acid, (cis-(1R))-isomer

Chemical Property of Phytomonic acid

Chemical Property:

• Vapor Pressure: 8E-08mmHg at 25°C
• Refractive Index: 1.47
• Boiling Point: 408.7°Cat760mmHg
• Flash Point: 180°C
• PSA: 37.30000
• Density: 0.923g/cm³
• LogP: 6.18840
• XLogP3: 7.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 15
• Exact Mass: 296.271530387
• Heavy Atom Count: 21
• Complexity: 262

Purity/Quality:

98%Min ^*data from raw suppliers

Phytomonic Acid ≥98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCCC1CC1CCCCCCCCCC(=O)O
• Description: Phytomonic 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.

Technology Process of Phytomonic acid

There total 38 articles about Phytomonic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 62.0%

(1R,2S)-2-hexyl-1-(10'-hydroxydec-1'-yl)cyclopropane (252009-75-9) → (11R,12S)-lactobacillic acid (503-06-0,58073-36-2,60761-43-5,84236-97-5,19625-10-6,83447-87-4)

Guidance literature:

With potassium permanganate; cetyltrimethylammonim bromide; In water; acetonitrile;

DOI:10.1016/S0040-4039(99)01378-7

Reference yield: 55.0%

methyl (Z)-10-(2-hexylcyclopropan-1-yl)decanoate (112418-57-2) → (11R,12S)-lactobacillic acid (503-06-0,58073-36-2,60761-43-5,84236-97-5,19625-10-6,83447-87-4)

Guidance literature:

With sodium hydroxide; In methanol; for 18h; Heating;

DOI:10.1016/S0957-4166(03)00165-4

Reference yield:

C19H34O2 → (±)-lactobacillic acid (503-06-0,19625-10-6,58073-36-2,60761-43-5,84236-97-5,83447-87-4)

Guidance literature:

With hydrazine hydrate; copper(II) sulfate; In ethanol; at 25 ℃;

DOI:10.1021/acs.orglett.8b01791

upstream raw materials:

cis-vaccenic acid

(1R,2S)-2-hexyl-1-(10'-hydroxydec-1'-yl)cyclopropane

methyl (Z)-10-(2-hexylcyclopropan-1-yl)decanoate

((1R,2S)-2-Hydroxymethyl-cyclopropyl)-methanol

Refernces

• 1、 Iwasaki, Takanori,Terahigashi, Shohei,Wang, Yufei,Tanaka, Arisa,Zhao, Hanqing,Fujimoto, Yukari,Fukase, Koichi,Kambe, Nobuaki. "Synthesis of Cyclopropane Fatty Acids by C(sp3)?C(sp3) Cross-Coupling Reaction and Formal Synthesis of α-Mycolic Acid". supporting information. p. 3810 - 3817. Retrieved 2018/09/18.
• 2、 Coxon, Geoffrey D.,Al-Dulayymi, Juma R.,Baird, Mark S.,Knobl, Stefan,Roberts, Evan,Minnikin, David E.. "The synthesis of (11R,12S)-lactobacillic acid and its enantiomer". . p. 1211 - 1222. Retrieved 2007/10/03.