PERICOSINE A

Base Information

• Chemical Name: PERICOSINE A
• CAS No.: 200335-68-8
• Molecular Formula: C8H11 Cl O5
• Molecular Weight: 222.62
• Hs Code.: 29419000
• Mol file: 200335-68-8.mol

Synonyms:(+)-PericosineA; Pericosine A

Chemical Property of PERICOSINE A

Chemical Property:

• Boiling Point: 367.0±42.0 °C(Predicted)
• PKA: 12.77±0.70(Predicted)
• PSA: 86.99000
• Density: 1.52±0.1 g/cm3(Predicted)
• LogP: -1.21050

Purity/Quality:

98%Min ^*data from raw suppliers

Pericosine A ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of PERICOSINE A

There total 20 articles about PERICOSINE A 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: 89.0%

methyl (3S,4R,5S,6S)-6-chloro-3,4-O-cyclohexylidene-3,4,5-trihydroxy-1-cyclohexene-1-carboxylate (1163681-01-3) → methyl (3S,4S,5S,6S)-6-chloro-3,4,5-trihydroxy-1-cyclohex-1-enecarboxylate (200335-68-8)

Guidance literature:

With methanol; trifluoroacetic acid; at 20 ℃; for 3h;

DOI:10.1021/ol9008188

Reference yield: 84.0%

methyl (3aS,6S,7S,7aS)-7-(acetyloxy)-6-chloro-2,2-dimethyl-3a,6,7,7a-tetrahydro-1,3-benzodioxole-5-carboxylate (1227264-30-3) → methyl (3S,4S,5S,6S)-6-chloro-3,4,5-trihydroxy-1-cyclohex-1-enecarboxylate (200335-68-8)

Guidance literature:

With methanol; acetyl chloride; at 20 ℃; for 12h;

DOI:10.1021/ol100525r

Reference yield: 63.0%

methyl (3S,4S,5S,6S)-6-chloro-5-O-tert-butyldimethylsilyl-3,4-O-cyclohexylidene-3,4,5-trihydroxy-1-cyclohexene-1-carboxylate (949159-87-9) → methyl (3S,4S,5S,6S)-6-chloro-3,4,5-trihydroxy-1-cyclohex-1-enecarboxylate (200335-68-8)

Guidance literature:

With trifluoroacetic acid; In methanol; at 0 ℃;

DOI:10.1021/jo070715l

upstream raw materials:

methyl (3S,4S,5S,6S)-6-chloro-5-O-tert-butyldimethylsilyl-3,4-O-cyclohexylidene-3,4,5-trihydroxy-1-cyclohexene-1-carboxylate

methyl (1R,2S,3R,4S,5R)-5-O-tert-butyldimethylsilyl-3,4-O-cyclohexylidene-1,2,3,4,5-pentahydroxycyclohexane-1-carboxylate

methyl (1R,2S,3R,4S,5R)-2-O-acetyl-5-O-tert-butyldimethylsilyl-3,4-O-cyclohexylidene-1,2,3,4,5-pentahydroxycyclohexane-1-carboxylate

methyl (1R,2R,3S,4R)-2-O-acetyl-3,4-O-cyclohexylidene-5-oxo-1,2,3,4-tetrahydroxycyclohexanecarboxylate

Downstream raw materials:

methyl (3R,4R,5R,6R)-3,4,5-trihydroxy-6-methoxy-1-cyclohexene-1-carboxylate

Refernces

An Electrophilic Natural Product Provides a Safe and Robust Odor Neutralization Approach to Counteract Malodorous Organosulfur Metabolites Encountered in Skunk Spray

10.1021/acs.jnatprod.9b00415

This research aimed to develop a safe and effective method for neutralizing the malodorous organosulfur compounds found in skunk spray using a naturally occurring electrophilic compound, pericosine A. The study demonstrated that pericosine A, derived from fungi, readily reacts with skunk-spray secretions to transform them into odorless products. Mechanistic and computational studies suggested that pericosine A and its synthetic analogues react with thiols and thioacetates under aqueous conditions to generate stable thioethers via SN2′-type mechanisms. The researchers found pericosine A to be non-irritating to skin and eyes and highly effective at deodorizing skunk anal gland secretions when formulated with cosmetic ingredients. Key chemicals used in the process included pericosine A, 2-phenylethanethiol, 4-bromo-α-toluene thioacetate, and spermine as a catalyst, with propylene glycol serving as a cosolvent. The study concluded that pericosine A and its analogues offer a promising, non-toxic approach to counteract noxious sulfur-containing chemicals, with potential applications in odor neutralization and the development of new materials to combat a range of malodorous substances.

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