Jalapinolic acid

Base Information

• Chemical Name: Jalapinolic acid
• CAS No.: 502-75-0
• Molecular Formula: C16H32O3
• Molecular Weight: 272.428
• Hs Code.: 2918199090
• DSSTox Substance ID: DTXSID60964533
• Nikkaji Number: J12.232G,J297.084H
• Wikidata: Q105351082
• Metabolomics Workbench ID: 1324
• Mol file: 502-75-0.mol

Synonyms:Jalapinolic acid;11-Hydroxyhexadecanoic acid;502-75-0;Jalapinoic acid;Builic acid;Hexadecanoic acid, 11-hydroxy-;11-hydroxy palmitic acid;11-hydroxy-hexadecanoic acid;jalapinolsaure;SCHEMBL316792;DTXSID60964533;(+)-11-Hydroxyhexadecanoic acid;LMFA01050049;AKOS040752149

Chemical Property of Jalapinolic acid

Chemical Property:

• Vapor Pressure: 2.06E-08mmHg at 25°C
• Boiling Point: 409.4°Cat760mmHg
• Flash Point: 215.6°C
• PSA: 57.53000
• Density: 0.955g/cm³
• LogP: 4.52310
• XLogP3: 5.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 14
• Exact Mass: 272.23514488
• Heavy Atom Count: 19
• Complexity: 204

Purity/Quality:

98%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCC(CCCCCCCCCC(=O)O)O

Technology Process of Jalapinolic acid

There total 4 articles about Jalapinolic 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:

scammonic acid A → D-quionovose (7658-08-4,478518-52-4) + L-Rhamnose (3615-41-6,478518-52-4) + D-glucose (50-99-7) + 11-hydroxyhexadecanoic acid (502-75-0)

Guidance literature:

With hydrogenchloride; water; In ethanol; for 1h; Reflux;

DOI:10.1016/j.bmcl.2009.06.087

Reference yield:

jalapinolic 11-O-α-L-rhamnopyranosyl-(1→3)-O-[4-O-n-dodecanoyl-α-L-rhamnopyranosyl-(1→4)]-O-[2-O-n-octanoyl]-α-L-rhamnopyranosyl-(1→4)-O-α-L-rhamnopyranosyl-(1→2)-O-β-D-fucopyranoside-(1,3''-lactone) → D-Fucose (3615-37-0,478518-52-4) + L-Rhamnose (3615-41-6,478518-52-4) + 11-hydroxyhexadecanoic acid (502-75-0)

Guidance literature:

jalapinolic 11-O-α-L-rhamnopyranosyl-(1→3)-O-[4-O-n-dodecanoyl-α-L-rhamnopyranosyl-(1→4)]-O-[2-O-n-octanoyl]-α-L-rhamnopyranosyl-(1→4)-O-α-L-rhamnopyranosyl-(1→2)-O-β-D-fucopyranoside-(1,3''-lactone); With sodium hydroxide; at 95 ℃; for 1h;

With hydrogenchloride; In water; butan-1-ol; at 95 ℃; for 1h;

DOI:10.1021/acs.jnatprod.1c00649

Reference yield:

1-hexadecylcarboxylic acid (57-10-3) → 11-hydroxyhexadecanoic acid (502-75-0) + 10-hydroxy-hexadecanoic acid (3422-30-8,23048-75-1,23048-82-0) + 9-hydroxyhexadecanoic acid (17833-52-2)

Guidance literature:

With cytochrome P₄₅₀ BM-3 enzyme mutant 9-10A-F₈₇A; Enzymatic reaction;

upstream raw materials:

1-hexadecylcarboxylic acid

Downstream raw materials:

methyl ester of 11-hydroxyhexadecanoic acid

3-methylbutyric acid

1,10-decanedioic acid

1-hexadecylcarboxylic acid