Lactobacillic acid

Base Information

• Chemical Name: Lactobacillic acid
• CAS No.: 19625-10-6
• Molecular Formula: C19H36O2
• Molecular Weight: 296.4879
• UNII: SVS08S87RL
• Nikkaji Number: J13.562C
• Wikidata: Q2823275
• Metabolomics Workbench ID: 1891
• Mol file: 19625-10-6.mol

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

Chemical Property of Lactobacillic acid

Chemical Property:

• Vapor Pressure: 8E-08mmHg at 25°C
• Melting Point: 29 °C
• Boiling Point: 408.7°Cat760mmHg
• PKA: 4.78±0.10(Predicted)
• 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% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCCC1CC1CCCCCCCCCC(=O)O
• Isomeric SMILES: CCCCCC[C@H]1C[C@H]1CCCCCCCCCC(=O)O
• Uses: (11R,12S)-Lactobacillic Acid is a component of bacterial membranes and can be detected in cows milk and cheese.

Technology Process of Lactobacillic acid

There total 38 articles about Lactobacillic 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、 Mato, Mauro,Herlé, Bart,Echavarren, Antonio M.. "Cyclopropanation by Gold- or Zinc-Catalyzed Retro-Buchner Reaction at Room Temperature". supporting information. p. 4341 - 4345. Retrieved 2018/07/29.
• 2、 Shah, Sayali,White, Jonathan M.,Williams, Spencer J.. "Total syntheses of cis-cyclopropane fatty acids: Dihydromalvalic acid, dihydrosterculic acid, lactobacillic acid, and 9,10-methylenehexadecanoic acid". . p. 9427 - 9438. Retrieved 2014/12/11.