88-84-6

Basic information

• Product Name: GUAIENE
• Synonyms: 1,2,3,4,5,6,7,8-octahydro-1,4-dimethyl-7-(1-methylethylidene)-,(1S-cis)-Azulene;1,2,3,4,5,6,7,8-octahydro-1,4-dimethyl-7-(1-methylethylidene)-azulen(1s-ci;1,2,3,4,5,6,7,8-Octahydro-1,4-dimethyl-7-(1-methylethylidene)-azulene;1,2,3,4,5,6,7,8-octahydro-1,4-dimethyl-7-(1-methylethylidene)-azulene,(1s,ci;1,4-Dimethyl-7-(1-methylethylidene)-1,2,3,4,5,6,7,8-octahydroazulene;Azulene, 1,2,3,4,5,6,7,8-octahydro-1,4-dimethyl-7-(1-methylethylidene)-, (1S-cis)-;azulene,1,2,3,4,5,6,7,8-octahydro-1,4-dimethyl-7-(1-methylethylidene)-,(1s,;beta-cis-Guaiene
• CAS NO: 88-84-6
• Molecular Formula: C₁₅H₂₄
• Molecular Weight: 204.35
• EINECS: 201-860-1
• Mol File: 88-84-6.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 277.87°C (rough estimate)
• Appearance: /
• Density: 0.8895 (estimate)
• Refractive Index: 1.5000 (estimate)
• Storage Temp.: Amber Vial, Refrigerator, Under inert atmosphere
• Solubility: Chloroform (Sparingly), Methanol (Slightly)
• CAS DataBase Reference: GUAIENE(CAS DataBase Reference)
• NIST Chemistry Reference: GUAIENE(88-84-6)
• EPA Substance Registry System: GUAIENE(88-84-6)

Safety Data

• Hazardous Substances Data: 88-84-6(Hazardous Substances Data)

Usage

Description

Guaiene has very little odor and a delicate, woody flavor. It is usually prepared by dehydrating guaiol with KHS04. This bicyclic sesquiterpene may be found naturally in patchouli oil and other essential oils in small quantities.

Chemical Properties

Guaiene has earthy and spicy aroma and a delicate, woody favor.

Occurrence

Guaiene is a bicyclic sesquiterpene found naturally in patchouli oil and other essential oils in small quantities Reported found in lime peel oil, peppermint oil, calamus, lovage root, seed and leaf and mangosteen (Garcinia mangostana L )

Uses

β-Guaiene is an essential oil extracted from natural sources and exhibits antimicrobial and antiparasitic activities

Preparation

Usually prepared by dehydrating guaiol with KHSO4.

InChI:InChI=1/C15H24/c1-10(2)13-7-5-11(3)14-8-6-12(4)15(14)9-13/h11-12H,5-9H2,1-4H3/t11-,12-/m0/s1

Upstream product

• 489-86-1 guaiol 

Relevant articles and documents

Effective analysis of rotundone at below-threshold levels in red and white wines using solid-phase microextraction gas chromatography/tandem mass spectrometry

Rotundone is an oxygenated sesquiterpene belonging to the family of guaianes, giving the 'peppery' aroma to white and black pepper and to red wines. Here we describe a novel, convenient protocol for the synthesis of rotundone, starting from a commercially available compound and requiring only two reaction steps, and an improved, faster method of GC separation (30min) with selective quantisation of rotundone using tandem mass spectrometry in multiple reaction monitoring (MRM) mode with d5-rotundone as internal standard. With limits of detection (LODs) of 1.5ng/L in white wine and 2.0ng/L in red wine, intraday repeatability CV values of 6% and 5% at 50ng/L and 500ng/L and interday repeatability CV values of 13% and 6% at 50ng/L and 500ng/L, respectively, the improved protocol provides the desired sensitivity and selectivity for routine analysis of rotundone in both white and red wines. Initial application of this method highlighted the presence of unexpectedly high concentrations of rotundone, thus explaining the origin of the distinctive peppery aroma in Schioppettino and Vespolina red wines and in Gruener Veltliner white wines.