65694-19-1

Basic information

• Product Name: fasciculol C
• Synonyms: fasciculol C;(24R)-5α-Lanost-8-ene-2α,3β,12α,21,24,25-hexaol
• CAS NO: 65694-19-1
• Molecular Formula: C30H52O6
• Molecular Weight: 508.73028
• Mol File: 65694-19-1.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 676.9°Cat760mmHg
• Flash Point: 279.9°C
• Appearance: /
• Density: 1.19g/cm³
• Vapor Pressure: 3.14E-21mmHg at 25°C
• Refractive Index: 1.575
• CAS DataBase Reference: fasciculol C(CAS DataBase Reference)
• NIST Chemistry Reference: fasciculol C(65694-19-1)
• EPA Substance Registry System: fasciculol C(65694-19-1)

Safety Data

• Hazardous Substances Data: 65694-19-1(Hazardous Substances Data)

Usage

InChI:InChI=1/C30H52O6/c1-26(2)22-10-9-19-20(28(22,5)15-21(32)25(26)35)14-24(34)30(7)18(12-13-29(19,30)6)17(16-31)8-11-23(33)27(3,4)36/h17-18,21-25,31-36H,8-16H2,1-7H3/t17-,18+,21+,22?,23+,24-,25-,28+,29-,30-/m0/s1

Upstream product

• 86894-29-3 crustulinol 
• 86894-26-0 2α-(3'-hydroxy-3'-methyl)glutaryl-3β-acetylcrustulinol 
• 86894-29-3 crustulinol 
• 86894-26-0 3-acetyl-2-(3'-hydroxy-3'-methyl)glutarylcrustulinol 
• 142407-55-4 3,21-diacetyl-2-(3'-hydroxy-3'-methyl)glutarylcrustulinol 
• 124-41-4 sodium methylate 

Downstream Products

• 99499-98-6 fasciculol C 2,3,21-tri-p-bromobenzoate 

Relevant articles and documents

Isolation, identification and pharmacological studies on three toxic metabolites from a mushroom, Hebeloma spoliatum

Three metabolites, tentatively named HS-A, -B and -C, were isolated from a mushroom, Hebeloma spoliatum, as the fatal toxic principles to mice. HS-A was identified as 3-acetyl-2-(3'-hydroxy-3'-methyl)glutarylcrustulinol, which has been isolated from Hebeloma crustuliniforme and H. sinapizans as a cytotoxic principle. HS-B and -C were deduced to be 3,21-diacetyl-2-(3'-hydroxy-3'-methyl)glutarylcrustulinol and 3-acetyl-2-(3'-hydroxy-3'-methyl)glutarylanhydrocrustulinol, respectively, from their chemical and spectral data. Intraperitoneal administration of HS-A, -B and -C at a dose of 100 mg/kg caused death after paralysis of the limbs in mice. The compounds caused relaxation of mouse small intestine contracted by acetylcholine chloride or barium chloride treatment in vitro. They appear to exhibit a paraverine-like relaxation effect.

Lanostane triterpenoids from the mushroom Naematoloma fasciculare

In our continuing search for structurally interesting and bioactive metabolites from Korean wild mushrooms, bioassay-guided fractionation and a chemical investigation of the MeOH extracts of the fruiting bodies of the mushroom Naematoloma fasciculare resulted in the isolation of four new lanostane triterpenoids (1-4), together with 11 known compounds (5-15). The structures of 1-5 were determined by a combination of 1D and 2D NMR and HRMS. The absolute configuration of the 3-hydroxy-3-methylglutaryl group as a side chain in 1 and 2 was determined by the alkaline methanolysis method. The full NMR data assignment of the known compound fasciculol G (5) is reported for the first time. Compounds 1-15 were tested for their antiproliferative activities against four human cancer cell lines (A549, SK-OV-3, SK-MEL-2, and HCT-15) and evaluated for their inhibitory effects on nitric oxide production in a lipopolysaccharide-activated murine microglial cell line.