2198-92-7

Basic information

• Product Name: VERRUCAROL
• Synonyms: 4BETA,15-DIHYDROXY-12,13-EPOXY-TRICHOTHEC-9-ENE;VERRUCAROL;4β,15-dihydroxy-12,13-epoxytrichothec-9-ene;12,13-Epoxytrichothec-9-ene-4β,15-diol;(4beta)-12,13-Epoxytrichothec-9-ene-4,15-diol;Trichothec-9-ene-4,15-diol, 12,13-epoxy-, (4beta)-
• CAS NO: 2198-92-7
• Molecular Formula: C₁₅H₂₂O₄
• Molecular Weight: 266.33
• Mol File: 2198-92-7.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 422°Cat760mmHg
• Flash Point: 209°C
• Appearance: /
• Density: 1.3g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.545
• Storage Temp.: −20°C
• CAS DataBase Reference: VERRUCAROL(CAS DataBase Reference)
• NIST Chemistry Reference: VERRUCAROL(2198-92-7)
• EPA Substance Registry System: VERRUCAROL(2198-92-7)

Safety Data

• Hazard Codes: T+
• Statements: 26/27/28-36/37/38
• Safety Statements: 22-26-36/37/39-45
• RIDADR: UN 2811 6.1/PG 1
• WGK Germany: 3
• Hazardous Substances Data: 2198-92-7(Hazardous Substances Data)

Usage

General Description

Verrucarol is a naturally occurring sesquiterpene alcohol, which is a type of organic compound found in various plants and fungi. It is known for its potent anti-inflammatory and antimicrobial properties, making it a valuable compound in medicine and agriculture. Verrucarol has been studied for its potential in treating various inflammatory and infectious diseases, such as skin conditions and respiratory infections. Its chemical structure and biological activity have made it a subject of interest for further research into its potential therapeutic applications. Additionally, verrucarol has shown promise as a natural fungicide, with potential use in controlling fungal diseases in crops.

InChI:InChI=1/C19H26O6/c1-11-5-6-18(9-22-12(2)20)15(7-11)25-16-8-14(24-13(3)21)17(18,4)19(16)10-23-19/h7,14-16H,5-6,8-10H2,1-4H3/t14-,15-,16-,17-,18-,19+/m1/s1

Upstream product

• 74072-83-6 roridin J 
• 3148-09-2 verrucarin A 
• 85124-22-7 roridin L-2 
• 2198-94-9 diacetyl verrucarol 
• 2270-40-8 anguidine 
• 204910-14-5 (3S,3aR,7aR)-3-[4-(tert-Butyl-diphenyl-silanyloxy)-butyryl]-3a-methoxymethoxymethyl-3,6-dimethyl-3a,4,5,7a-tetrahydro-3H-benzofuran-2-one 
• 200420-37-7 (3S,3aR,7aR)-3-[(R)-4-(tert-Butyl-diphenyl-silanyloxy)-1-hydroxy-butyl]-3a-methoxymethoxymethyl-3,6-dimethyl-3a,4,5,7a-tetrahydro-3H-benzofuran-2-one 
• 200420-57-1 (3S,3aR,7aR)-3-[(S)-4-(tert-Butyl-diphenyl-silanyloxy)-1-hydroxy-butyl]-3a-methoxymethoxymethyl-3,6-dimethyl-3a,4,5,7a-tetrahydro-3H-benzofuran-2-one 
• 200420-45-7 Acetic acid (1R,3S,3aR,4aR,8aR,8bS)-3a-(tert-butyl-dimethyl-silanyloxy)-1-methoxymethoxy-8a-methoxymethoxymethyl-6,8b-dimethyl-2,3,3a,4a,7,8,8a,8b-octahydro-1H-benzo[b]cyclopenta[d]furan-3-yl ester 
• 200420-42-4 (1R,3R,3aS,4aR,8aR,8bS)-3a-(tert-Butyl-dimethyl-silanyloxy)-1-methoxymethoxy-8a-methoxymethoxymethyl-6,8b-dimethyl-2,3,3a,4a,7,8,8a,8b-octahydro-1H-benzo[b]cyclopenta[d]furan-3-carboxylic acid methyl ester 
• 200421-22-3 (1R,3S,3aS,4aR,8aR,8bS)-3a-(tert-Butyl-dimethyl-silanyloxy)-1-methoxymethoxy-8a-methoxymethoxymethyl-6,8b-dimethyl-2,3,3a,4a,7,8,8a,8b-octahydro-1H-benzo[b]cyclopenta[d]furan-3-carboxylic acid methyl ester 
• 200420-54-8 (1R,3S,3aR,4aR,8aR,8bS)-3a-(tert-Butyl-dimethyl-silanyloxy)-1-methoxymethoxy-8a-methoxymethoxymethyl-6,8b-dimethyl-2,3,3a,4a,7,8,8a,8b-octahydro-1H-benzo[b]cyclopenta[d]furan-3-ol 
• 334934-61-1 (1R,3aR,4aR,8aR,8bS)-3a-(tert-Butyl-dimethyl-silanyloxy)-1-methoxymethoxy-8a-methoxymethoxymethyl-6,8b-dimethyl-2,3,3a,4a,7,8,8a,8b-octahydro-1H-benzo[b]cyclopenta[d]furan-3-ol 
• 200420-46-8 Methanesulfonic acid (1R,3S,3aR,4aR,8aR,8bS)-3a-(tert-butyl-dimethyl-silanyloxy)-1-methoxymethoxy-8a-methoxymethoxymethyl-6,8b-dimethyl-2,3,3a,4a,7,8,8a,8b-octahydro-1H-benzo[b]cyclopenta[d]furan-3-yl ester 

Downstream Products

• 76685-83-1 Trichoverrol B 
• 76685-82-0 trichoverrin B 
• 82521-42-4 C₅₇H₈₆O₉Si₃ 
• 84303-84-4 C₂₅H₃₇O₁₀P 
• 84303-92-4 Verrucarin J seco acid 
• 4513-00-2 C₂₁H₃₀O₆ 
• 4513-00-2 C₂₁H₃₀O₆ 
• 78501-53-8 4-O-(5'-phenacyloxycarbonylpentanoyl)-15-O-<5'-O-(tetrahydro-2''-pyranyl)mevalonyl>verrucarol 
• 78501-73-2 15-O-<5'-O-(5''-phenacyloxycarbonyl-pentanoyl)mevalonyl>-4-O-(tetrahydro-2'-pyranyl)verrucarol 
• 2198-94-9 4,15-di-O-diacetyl-4-epiverrucarol 
• 84303-90-2 C₂₇H₄₄O₆Si 
• 84303-90-2 C₂₇H₄₄O₆Si 
• 84303-91-3 12,13-Epoxytrichothec-9-ene-4β,15-diol 15-<5'-<(1,1-Dimethylethyl)dimethylsilyloxy>-3'-methyl-2'(E)-pentenoate> 
• 84303-90-2 12,13-Epoxytrichothec-9-ene-4β,15-diol 15-<5'-<(1,1-Dimethylethyl)dimethylsilyloxy>-3'-methyl-2'(E)-pentenoate> 

Relevant articles and documents

Synthesis of verrucarin A and 3α-hydroxyverrucarin A from verrucarol and diacetoxyscripenol (Anguidine)

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Total synthesis of (-)-verrucarol

We have achieved the total synthesis of (-)-verrucarol, a trichothecene sesquiterpenoid obtained as a hydrolysis product of the naturally occurring verrucarin A. Our total synthesis began with the previously reported enantiometrically pure bicyclic α-methylated γ-lactone, which was prepared from D-glucose. The key steps for the total synthesis were (1) aldol-like carbon-carbon bond formation applied to the starting lactone using a four- carbon aldehyde as an electrophile for introduction of the quaternary stereogenic carbon sharing the B and C-rings of the trichothecene skeleton, (2) Dieckmann cyclization of the derived ε-ester lactone for construction of the C-ring equivalent, (3) Barton's decarboxylative oxygenation for conversion of a carboxylic acid functionality in the Dieckmann cyclization product into a hydroxyl group, (4) skeletal enlargement strategy for the crucial trichothecene skeleton construction, and (5) the final stereoselective formation of the exo-epoxy ring at the methylene carbon in the bridge constituting the B and C-rings.

RORIDIN L-2, A NEW TRICHOTHECENE

The structure (2) of roridin L-2 is shown to be a C29-trichothecene that lacks the macrocyclic lactone system usually present in the roridins.