Hopane

Base Information

• Chemical Name: Hopane
• CAS No.: 471-62-5
• Molecular Formula: C₃₀H₅₂
• Molecular Weight: 412.743
• Hs Code.: 2929101000
• UNII: W2H93796GT
• DSSTox Substance ID: DTXSID00904337
• Nikkaji Number: J12.030H
• Wikipedia: Hopane
• Wikidata: Q5898987
• Metabolomics Workbench ID: 55388
• Mol file: 471-62-5.mol

Synonyms:hopane;hopane, (17alpha)-isomer;hopane, (21beta)-isomer

Chemical Property of Hopane

Chemical Property:

• Vapor Pressure: 4.06E-08mmHg at 25°C
• Refractive Index: 1.497
• Boiling Point: 457.4 °C at 760 mmHg
• Flash Point: 221.8 °C
• PSA: 0.00000
• Density: 0.925 g/cm³
• LogP: 9.13390
• Storage Temp.: 2-8°C
• XLogP3: 11.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 1
• Exact Mass: 412.406901659
• Heavy Atom Count: 30
• Complexity: 688

Purity/Quality:

99% ^*data from raw suppliers

17β(H),21β(H)-Hopane solution 0.1?mg/mL in isooctane, analytical standard ^*data from reagent suppliers

Safty Information:

• Pictogram(s): F,Xn,N
• Hazard Codes: F,Xn,N
• Statements: 11-38-50/53-65-67
• Safety Statements: 60-61-62-33-29-16-9

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)C1CCC2(C1CCC3(C2CCC4C3(CCC5C4(CCCC5(C)C)C)C)C)C
• Isomeric SMILES: CC(C)[C@H]1CC[C@]2([C@H]1CC[C@@]3([C@@H]2CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CCCC5(C)C)C)C)C)C

Technology Process of Hopane

There total 22 articles about Hopane 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: 90.0%

1,4-bis-O-benzyl-2,3-O-isopropylidene-5-aldehydo-D-ribitol (934356-93-1) + 30-phenylthiohopane (934356-90-8) → C52H78O5 + hopane (471-62-5,1176-44-9,13849-96-2,33281-23-1,50894-70-7)

Guidance literature:

30-phenylthiohopane; With 4,4'-di(tert-butyl)-[1,1-biphenyl]yllithium; In tetrahydrofuran;

1,4-bis-O-benzyl-2,3-O-isopropylidene-5-aldehydo-D-ribitol; In tetrahydrofuran; Further stages.;

DOI:10.1002/chem.200600659

Reference yield: 86.0%

30-phenylthiohopane (934356-90-8) + benzyl 2,3-O-isopropylidene-β-D-ribo-pentodialdo-1,4-furanoside (155681-03-1) → C45H70O5 + hopane (471-62-5,1176-44-9,13849-96-2,33281-23-1,50894-70-7)

Guidance literature:

30-phenylthiohopane; With 4,4'-di(tert-butyl)-[1,1-biphenyl]yllithium; In tetrahydrofuran;

benzyl 2,3-O-isopropylidene-β-D-ribo-pentodialdo-1,4-furanoside; In tetrahydrofuran; Further stages.;

DOI:10.1002/chem.200600659

Reference yield: 81.0%

30-phenylthiohopane (934356-90-8) + (3aR,4S,6R,6aR)-tetrahydro-6-methoxy-2,2-dimethylfuro-[3,4-d][1,3]dioxole-4-carbaldehyde (33985-40-9) → C39H66O5 + hopane (471-62-5,1176-44-9,13849-96-2,33281-23-1,50894-70-7)

Guidance literature:

30-phenylthiohopane; With 4,4'-di(tert-butyl)-[1,1-biphenyl]yllithium; In tetrahydrofuran; at -78 ℃; for 0.05h;

(3aR,4S,6R,6aR)-tetrahydro-6-methoxy-2,2-dimethylfuro-[3,4-d][1,3]dioxole-4-carbaldehyde; In tetrahydrofuran; at 20 ℃; Further stages.;

DOI:10.1002/chem.200600659

upstream raw materials:

(4S,5R)-4-Benzyloxymethyl-2,2-dimethyl-5-(R)-oxiranyl-[1,3]dioxolane

1,4-bis-O-benzyl-2,3-O-isopropylidene-5-aldehydo-D-ribitol

30-phenylthiohopane

benzyl 2,3-O-isopropylidene-β-D-ribo-pentodialdo-1,4-furanoside

Downstream raw materials:

21αH-Hopan

Hop-17⁽²¹⁾-ene

17α,21α-Hopan

C₃₀H₄₆S

Refernces

UNEXPECTED REGIOSPECIFICITY IN PHOTOCHEMICAL α-CLEAVAGE OF HYDRINDANONES.

10.1016/S0040-4039(01)91553-9

The research investigates the unexpected regiospecificity in the photochemical α-cleavage of hydrindanones derived from triterpenes. The study focuses on the photolysis of trans- and cis-hydrindanones, specifically compounds like 22,29,30-trinorhopan-21-one and 22,29,30-trinor-(17aH)-hopan-21-one in the hopane series, and analogous compounds in the lupane series. The trans-hydrindanones were found to cleave predominantly on the least substituted side of the carbonyl group, yielding unsaturated aldehydes, while the cis-hydrindanones cleaved on the more highly substituted side, resulting in methyl esters. The regiospecificity was shown to be strictly stereochemistry-dependent. The chemicals involved in the research include the starting materials such as hopane and lupane precursors, solvents like degassed anhydrous methanol, and the reaction products like unsaturated aldehydes and methyl esters. The study utilized techniques such as capillary gas chromatography and GC-mass spectrometry for analysis. The findings suggest that pure compounds can be obtained in high yields through this photoinduced cleavage, which could have synthetic applications. Further investigations into the kinetic aspects and quantum efficiencies of these reactions are proposed to elucidate the underlying mechanisms.