6890-88-6

Basic information

• Product Name: ebericol
• Synonyms: ebericol;24-Methylene-24-dihydrolanosterol;24-Methylene-5α-lanost-8-en-3β-ol;24-Methylenelanost-8-en-3β-ol;24-Methylenelanosterol;Obtusifoldienol
• CAS NO: 6890-88-6
• Molecular Formula: C₃₁H₅₂O
• Molecular Weight: 440.74398
• Mol File: 6890-88-6.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 506.4°C at 760 mmHg
• Flash Point: 225.7°C
• Appearance: /
• Density: 0.97g/cm³
• Vapor Pressure: 2.25E-12mmHg at 25°C
• Refractive Index: 1.524
• CAS DataBase Reference: ebericol(CAS DataBase Reference)
• NIST Chemistry Reference: ebericol(6890-88-6)
• EPA Substance Registry System: ebericol(6890-88-6)

Safety Data

• Hazardous Substances Data: 6890-88-6(Hazardous Substances Data)

Usage

Definition

ChEBI: A natural product found in Taiwanofungus camphoratus.

InChI:InChI=1/C31H52O/c1-20(2)21(3)10-11-22(4)23-14-18-31(9)25-12-13-26-28(5,6)27(32)16-17-29(26,7)24(25)15-19-30(23,31)8/h20,22-23,26-27,32H,3,10-19H2,1-2,4-9H3/t22-,23-,26?,27+,29-,30-,31+/m1/s1

Upstream product

• 14787-39-4 3β-acetoxy-24-methylene-lanost-8-ene 
• 13879-13-5 lanosta-8,24-dien-3-one 
• 79-63-0 tirucallol 
• 14031-35-7 S-Adenosyl-L-methionine 
• 19044-12-3 lanosterol 

Downstream Products

• 14787-39-4 3-O-Acetyl-euphorbol 
• 101848-33-3 24-methylene-24(25)-dihydrolanosten-3-one 
• 14787-39-4 3β-acetoxy-24-methylene-lanost-8-ene 
• 16763-86-3 O-Benzoyl-euphorbol 
• 50-00-0 formaldehyd 
• 64-18-6 formic acid 

Relevant articles and documents

Sterol C24-methyltransferase: Physio- and stereo-chemical features of the sterol C3 group required for catalytic competence

Sterol C24-methyltransferases (24-SMTs) catalyze the electrophilic alkylation of Δ24-sterols to a variety of sterol side chain constructions, and the C3- moiety is the primary determinant for substrate binding by these enzymes. To determine what specific structural features of the C3-polar group ensure sterol catalysis, a series of structurally related C3-analogs of lanosterol that differed in stereochemistry, bulk and electronic properties were examined against the fungal 24-SMT from Paracoccidioides brasiliensis (Pb) which recognize lanosterol as the natural substrate. Analysis of the magnitude of sterol C24-methylation activity (based on the kinetic constants of Vmax/Km and product distributions determined by GC-MS) resulting from changes at the C3-position in which the 3β-OH was replaced by 3α-OH, 3β-acetyl, 3-oxo, 3-OMe, 3β-F, 3β-NH2 (protonated species) or 3H group revealed that lanosterol and five substrate analogs were catalyzed and yielded identical side chain products whereas neither the 3H- or 3α-OH lanosterol derivatives were productively bound. Taken together, our results demonstrate a chemical complementarity involving hydrogen bonding formation of specific active site contacts to the nucleophilic C3-group of sterol is required for proper orientation of the substrate C-methyl intermediate in the activated complex.

EFFECT ON ERGOSTEROL BIOSYNTHESIS OF A FUNGICIDE, SSF-109, IN BOTRYTIS CINEREA

Treatment of Botrytis cinerea with a novel fungicide SSF-109, (dl)-cis-1-(4-chlorophenyl)-2-(1H-1,2,4-triazol-1-yl)cyclo-heptanol (0.45 μg ml-1), gave five 14α-methyl sterols, 24-methylene-24(25)-dihydrolanosterol, 24-methylene-24(25)-dihydrolanosten-3-one, obtusifoliol, obtusifolione, and 14α-methylfecosterol, together with ergosterol and ergosta-5,8,22-trien-3β-ol.SSF-109 was found to inhibit the biosynthesis of ergosterol at the 14α-demethylation step.