6750-60-3

Basic information

• Product Name: spathulenol,(+)-spathulenol,espatulenol
• Synonyms: spathulenol,(+)-spathulenol,espatulenol;SPATHULENOL;(1aR,4aβ,7aα,7bβ)-Decahydro-1,1,7-trimethyl-4-methylene-1H-cycloprop[e]azulen-7α-ol;Espatulenol;[1ar-(1aà,4aà,7á,7aá,7bà)]-Decahydro-1,1,7-trimethyl-4-methylene-1H-cycloprop[e]azulen-7-ol;Spathulel;Spathulrnol
• CAS NO: 6750-60-3
• Molecular Formula: C₁₅H₂₄O
• Molecular Weight: 220.35046
• Mol File: 6750-60-3.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 297°C at 760 mmHg
• Flash Point: 123.9°C
• Appearance: /
• Density: 1.02g/cm³
• Vapor Pressure: 0.000141mmHg at 25°C
• Refractive Index: 1.527
• PKA: 15.10±0.40(Predicted)
• CAS DataBase Reference: spathulenol,(+)-spathulenol,espatulenol(CAS DataBase Reference)
• NIST Chemistry Reference: spathulenol,(+)-spathulenol,espatulenol(6750-60-3)
• EPA Substance Registry System: spathulenol,(+)-spathulenol,espatulenol(6750-60-3)

Safety Data

• Hazardous Substances Data: 6750-60-3(Hazardous Substances Data)

Usage

Description

Spathulenol?is a tricyclic?sesquiterpene?alcohol which has a basic skeleton similar to the?azulenes,it occurs in?oregano?among other plants.

Appearance

Spathulenol is a colorless to pale yellow clear liquid.

Biological activity

Spathulenol is isolated from psidium guineense Sw, has antioxidant, anti-inflammatory, anti-proliferative and anti-mycobacterial activities. It shows high antioxidant activity in DPPH system with IC50 of 85.60 μg/mL.

Uses

Eucalyptol is an organic alcohol compound, mainly used for content determination and experimental research, not for other purposes.

InChI:InChI=1/C15H24O/c1-9-5-6-11-13(14(11,2)3)12-10(9)7-8-15(12,4)16/h10-13,16H,1,5-8H2,2-4H3/t10-,11+,12+,13+,15-/m0/s1

Upstream product

• 32543-79-6 (1S,3R)-2,2-dimethyl-3-(3-oxobutyl)cyclopropane-1-carbaldehyde 
• 4497-92-1 2-carene 
• 41437-00-7 (+)-bicyclogermacrene 
• 489-39-4 (+)-aromadendrene 
• 99147-41-8 (1aR,4aR,7R,7aS,7bS)-1,1,7-Trimethyldecahydro-4H-cyclopropa[e]azulen-4-one 
• 6790-66-5 (-)-apoaromadendrone 
• 73809-82-2 (1S,3aR,8aS)-3a-methyl-7-methylidene-1-propan-2-yl-2,3,5,6,8,8a-hexahydro-1H-azulen-4-one 
• 99147-42-9 (+)-11β-hydroxy-apoaromadendrone 
• 2344-80-1 Chloromethyltrimethylsilane 
• 19493-09-5 Methylenetriphenylphosphorane 

Downstream Products

• 53526-64-0 β-Spathulen 
• 70000-15-6 4β,10β-aromadendranediol 
• 70051-38-6 4β,10α-aromadendranediol 

Relevant articles and documents

Biomimetic synthesis of (+)-ledene, (+)-viridiflorol, (-)-palustrol, (+)-spathulenol, and psiguadial A, C, and D via the platform terpene (+)-bicyclogermacrene

(+)-Bicyclogermacrene is a strained bicyclic and common sesquiterpene found in several essential oils. A short and good yielding synthesis of bicyclogermacrene proceeding in seven steps is reported. This terpene is used as key platform intermediate for a biomimetic access to several aromadendrene sesquiterpenoids, such as ledene, viridiflorol, palestrol, and spathulenol. Furthermore, bicyclogermacrene is shown to be the terpene component in the synthesis of the meroterpenoids psiguadial A, C, and D. Let nature be your guide! A concise synthesis of the terpene (+)-bicyclogermacrene enables its use as a platform for a fast access to a range of different terpenoids of the aromadendrene family and meroterpenoids of the psiguadial family (see scheme).

FIRST PREPARATION OF (+)-SPATHULENOL. REGIO- AND STEREOSELECTIVE OXIDATION OF (+)-AROMADENDRENE WITH OZONE.

(+)-Spathulenol was prepared for the first time in three reaction steps from (+)-aromadendrene by two subsequent ozonizations the second of which was regio- and stereoselective, followed by a wittig reaction.The overall recycle yield was 13percent.