Hopane-3β,22-diol

Base Information

• Chemical Name: Hopane-3β,22-diol
• CAS No.: 22149-65-1
• Molecular Formula: C₃₀H₅₂O₂
• Molecular Weight: 444.742
• Mol file: 22149-65-1.mol

Synonyms:

Chemical Property of Hopane-3β,22-diol

Chemical Property:

• Melting Point: 284-285 °C(Solv: chloroform (67-66-3); methanol (67-56-1))
• Boiling Point: 515.6±23.0 °C(Predicted)
• PKA: 15.11±0.29(Predicted)
• Density: 1.014±0.06 g/cm3(Predicted)

Purity/Quality:

98% ^*data from raw suppliers

Hopane-3beta,22-diol ≥98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Hopane-3β,22-diol

There total 4 articles about Hopane-3β,22-diol 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:

squalene 2,3(S)-oxide (54910-48-4,54274-53-2,71606-52-5) → 21βH-hopane-3β,22-diol (22149-65-1) + (-)-achilleol A (125287-06-1) + 3β-hydroxy-hop-22(29)-ene (58801-23-3)

Guidance literature:

With cell-free homogenate of E_. coli after SHC D₃₇₇C expression; citric acid; In water; at 60 ℃; pH=6.0; Enzymatic reaction;

DOI:10.1271/bbb.63.2189

Reference yield:

(3S)-2,3-oxidosqualene (54274-53-2,71606-52-5) + (3R)-2,3-oxidosqualene (54274-53-2,71606-52-5) → 21βH-hopane-3β,22-diol (22149-65-1) + 3β-hydroxy-hop-22(29)-ene (58801-23-3) + 3α-hydroxyhopene + 3α-3,22-dihydroxyhopane

Guidance literature:

With squalene-hopene cyclase; In aq. buffer; at 55 ℃; for 20h; pH=6; Enzymatic reaction;

DOI:10.1039/c8ob02009d

Reference yield:

2,3-oxidosqualene → 21βH-hopane-3β,22-diol (22149-65-1) + 3β-hydroxy-hop-22(29)-ene (58801-23-3) + 3α-hydroxyhopene + 3α-3,22-dihydroxyhopane

Guidance literature:

With Alicyclobacillus acidocaldarius squalene-hopene cyclase; In aq. buffer; at 45 ℃; for 12h; Enzymatic reaction;

DOI:10.1002/cbic.201800281

upstream raw materials:

squalene 2,3(S)-oxide

(3S)-2,3-oxidosqualene

(3R)-2,3-oxidosqualene

Downstream raw materials:

(3S,3aS,5aR,5bR,11aR,11bR,13aR,13bS)-3-(1-Hydroxy-1-methyl-ethyl)-5a,5b,8,8,11a,13b-hexamethyl-icosahydro-cyclopenta[a]chrysen-9-one

hop-17(21)-en-3-ol

hydroxyhopanone

Refernces

• 1、 Fukuda, Yoriyuki,Watanabe, Takashi,Hoshino, Tsutomu. "Mutated variants of squalene-hopene cyclase: Enzymatic syntheses of triterpenes bearing oxygen-bridged monocycles and a new 6,6,6,6,6-fusded pentacyclic scaffold, named neogammacerane, from 2,3-oxidosqualene". supporting information. p. 6987 - 7000. Retrieved 2018/10/02.
• 2、 Sato, Tsutomu,Hoshino, Tsutomu. "Functional analysis of the DXDDTA motif in squalene-hopene cyclase by site-directed mutagenesis experiments: Initiation site of the polycyclization reaction and stabilization site of the carbocation intermediate of the initially cyclized A-ring". . p. 2189 - 2198. Retrieved 2007/10/03.