546-79-2

Basic information

• Product Name: 4-THUJANOL
• Synonyms: (E)-Sabinene hydrate;(Z)-Sabinene hydrate;2-methyl-5-(1-methylethyl)-bicyclo[3.1.0]hexan-2-o;2-methyl-5-(1-methylethyl)-Bicyclo[3.1.0]hexan-2-ol;2-Methyl-5-(1-methylethyl)bicyclo[3.1.0]hexan-2-ol;Bicyclo[3.1.0]hexan-2-ol,2-methyl-5-(1-methylethyl)-;cis-Sabinenehydrate;c-sabinene hydrate
• CAS NO: 546-79-2
• Molecular Formula: C₁₀H₁₈O
• Molecular Weight: 172.26
• EINECS: 208-911-7
• Mol File: 546-79-2.mol
• Article Data: 6

Chemical Properties

• Melting Point: 58-62 °C
• Boiling Point: 201.7°Cat760mmHg
• Flash Point: 80.1°C
• Appearance: /
• Density: 1.03g/cm³
• Vapor Pressure: 0.0746mmHg at 25°C
• Refractive Index: 1.522
• Storage Temp.: ?20°C
• Solubility: Chloroform, Ethanol (Slightly), Hexanes (Slightly)
• PKA: 15.22±0.40(Predicted)
• CAS DataBase Reference: 4-THUJANOL(CAS DataBase Reference)
• NIST Chemistry Reference: 4-THUJANOL(546-79-2)
• EPA Substance Registry System: 4-THUJANOL(546-79-2)

Safety Data

• WGK Germany: 3
• F: 8-10-23
• Hazardous Substances Data: 546-79-2(Hazardous Substances Data)

Usage

Chemical Properties

Thujan-4-ol has an odor reminiscent of terpineol.

Occurrence

Reported found in peppermint oil (trans-form), lemon juice, mandarin peel oil, mandarin, nutmeg, peppermint, rosemary, scotch spearmint, tarragon, thyme, black currant (buds), Vitis vinifera L., ginger, spearmint oil, other Mentha oils, pepper, sweet marjoram, cardamom, origanum, dill herb, Oscimum basilicum varieties and laurel.

Uses

Sabinene Hydrate is a monoterpene and an essential oil component, found to have antifungal activity.

Aroma threshold values

Aroma characteristics at 1.0%: earthy camphoreous pine and turpentine-like with citrus grapefruit nuances.

Taste threshold values

Taste characteristics at 5 ppm: woody, citrus orange and grapefruit-like.

Synthesis

The Grignard reaction with sabina ketone yields two isomers, of which one is identical to an alcohol isolated from American peppermint oil; synthetic routes for the preparation of both the cis- and trans-form are also available.

InChI:InChI=1/C10H18O/c1-7(2)10-5-4-9(3,11)8(10)6-10/h7-8,11H,4-6H2,1-3H3/t8-,9+,10+/m0/s1

Upstream product

• 75-11-6 diiodomethane 
• 1619-28-9 3-isopropyl-cyclopent-2-enone 
• 917-54-4 methyllithium 
• 15826-79-6 1-isopropylbicyclo[3.1.0]hexan-4-ol 
• 13901-85-4 6-methyl-2,5-heptanedione 
• 68677-08-7 epoxisabinene 
• 74-95-3 1,1-dibromomethane 
• 39725-36-5 7-Hydroxysabina-ketone 
• 39725-37-6 1-Isopropenylbicyclo<3.1.0>hexan-4-one 
• 39725-31-0 2,2-dimethyl-1-oxaspiro[2.5]octan-6-one 
• 259210-13-4 3,7-dimethyl-6-phenylthio-1,7-octadien-3-ol 
• 259210-11-2 5-iodo-2-methyl-3-phenylthio-1-pentene 
• 134706-36-8 (+/-)-4-Methyl-3-phenylthio-4-penten-1-ol 

Relevant articles and documents

CYCLOPROPANATION PROCESS

A method for the preparation of cyclopropyl carbinols by cyclopropanation of unsaturated alcoholates, utilising a reagent system selected from (A) magnesium metal and dibromomethane, and (B) dibromomethane and a tertiary Grignard reagent, the reaction being carried out in the presence of an ether solvent. The process is useful, for example, for the preparation of ingredients for the flavour and fragrance industry.

Tandem cyclopropanation with dibromomethane under Grignard conditions

(Chemical Equation Presented) Tertiary Grignard reagents and dibromomethane efficiently cyclopropanate allylic (and certain homoallylic) magnesium and lithium alcoholates at ambient temperature in ether solvents. Lithium (homo)allyl alcoholates are directly cyclopropanated with magnesium and CH 2Br2 under Barbier conditions at higher temperatures. The reaction rates depend on the substitution pattern of the (homo)allylic alcoholates and on the counterion with lithium giving best results. Good to excellent syn-selectivities are obtained from α-substituted substrates, which are in accord with a staggered Houk model. In tandem reactions, cyclopropyl carbinols are obtained from allyloxylithium or -magnesium intermediates, generated in situ by alkylation of conjugated aldehydes, ketones, and esters as well as from allyl carboxylates or vinyloxiranes. Using this methodology, numerous fragrance ingredients and their precursors were efficiently converted to the corresponding cyclopropyl carbinols.

A short and efficient synthesis of (±)-trans-sabinene hydrate

A short synthesis of sabinene hydrate is reported. It uses cheap starting materials and affordable reagents. The main product of the synthesis is trans-sabinene hydrate.