498-16-8

Basic information

• Product Name: LAVANDULOL
• Synonyms: (-)-4-hexen-1-o;(r)-4-hexen-1-o;(r)-5-methyl-2-(1-methylethenyl)-4-hexen-1-ol;(R)-Lavandulol;(theta)-4-hexen-1-o;4-Hexen-1-ol, 2-isopropenyl-5-methyl-, (-)-;4-Hexen-1-ol, 5-methyl-2-(1-methylethenyl)-, (R)-;LAVANDULOL
• CAS NO: 498-16-8
• Molecular Formula: C₁₀H₁₈O
• Molecular Weight: 154.25
• Mol File: 498-16-8.mol
• Article Data: 14

Chemical Properties

• Boiling Point: 230.2°Cat760mmHg
• Flash Point: 88.3°C
• Appearance: /
• Density: 0.857g/cm³
• Vapor Pressure: 0.0127mmHg at 25°C
• Refractive Index: 1.461
• PKA: 14.81±0.10(Predicted)
• CAS DataBase Reference: LAVANDULOL(CAS DataBase Reference)
• NIST Chemistry Reference: LAVANDULOL(498-16-8)
• EPA Substance Registry System: LAVANDULOL(498-16-8)

Safety Data

• Hazardous Substances Data: 498-16-8(Hazardous Substances Data)

Usage

Definition

ChEBI: A monoterpenoid alcohol that is hepta-1-5-diene which is substituted at positions 2 and 6 by methyl groups and at position 3 by a hydroxymethyl group. It is commonly found in lavender oil.

InChI:InChI=1/C10H18O/c1-8(2)5-6-10(7-11)9(3)4/h5,10-11H,3,6-7H2,1-2,4H3/t10-/m0/s1

Upstream product

• 59550-37-7 (2R)-Benzoesaeure(2-isopropenyl-5-methyl-4-hexenyl)ester 
• 108-05-4 vinyl acetate 
• 58461-27-1 (+/-)-lavandulol 
• 25905-14-0 lavandulyl acetate 
• 108-30-5 succinic acid anhydride 
• 3350-78-5 3,3-Dimethylacryloyl chloride 
• 1327155-02-1 (R)-2-isopropenyl-5-methyl-hexane-1,5-diol 
• 1345866-27-4 C₁₂H₂₂O₃ 
• 1327155-05-4 (5S)-5-isopropenyl-2-methyl-octane-2,7-diol 
• 1327155-06-5 C₁₂H₂₂O₂ 
• 7086-79-5 (3S)-4-methyl-3-(3-oxobutyl)pent-4-enal 
• 557786-93-3 lavandulyl diphosphate 
• 130506-49-9 (+)-(3R,4'S)-3-(2',2'-dimethyl-1',3'-dioxolan-4'-yl)-4-methylpent-4-enol 
• 81997-76-4 (S,E)-3-(2,2-dimethyl-1,3-dioxolan-4-yl)-2-methylpropionic acid ethyl ester 

Downstream Products

• 41884-28-0 (R)-(+)-Tetrahydrolavandulol 
• 25905-14-0 lavandulyl acetate 
• 1608997-27-8 (R)-lavandulyl 3-methyl-3-butenoate 
• 2387-23-7 1,3-Dicyclohexylurea 
• 20777-39-3 (-)-(R)-lavanduyl acetate 
• 60244-53-3 ((2E,4E)-(S)-6-Isopropenyl-3,9-dimethyl-deca-2,4,8-trienyl)-triphenyl-phosphonium; bromide 
• 73365-71-6 ((2E,4E)-(R)-6-Isopropyl-3,9-dimethyl-deca-2,4-dienyl)-triphenyl-phosphonium; bromide 
• 6544-40-7 lavandulal 

Relevant articles and documents

Photocatalytic Transfer Hydrogenolysis of Allylic Alcohols on Pd/TiO2: A Shortcut to (S)-(+)-Lavandulol

We report herein a regio- and stereoselective photocatalytic hydrogenolysis of allylic alcohols to form unsaturated hydrocarbons employing a palladium(II)-loaded titanium oxide; the reaction proceeds at room temperature under light irradiation without stoichiometric generation of salt wastes. Olefin and saturated alcohol moieties tolerated the reaction conditions. Hydrogen atoms were selectively incorporated into less sterically congested carbons of the allylic functionalities. This protocol allowed a short-step synthesis of (S)-(+)-lavandulol from (R)-(?)-carvone by avoiding otherwise necessary protection/deprotection steps.

Fungal mediated kinetic resolution of racemic acetates to (R)-alcohols using Fusarium proliferatum

Fungal mediated kinetic resolution of seven acyclic/aromatic acetates was achieved using Fusarium proliferatum to furnish (R)-alcohols in high enantiomeric excess (>95%). The kinetic resolution was established as one-pot two-step de-esterification/oxidation biocatalytic process. Further, the preparative scale synthesis of (R)-(+)-1-phenylethanol was accomplished through de-esterification/oxidation of (±)-1-phenylethyl acetate using the whole cell of F. proliferatum NCIM 1105.

A Synthesis of (-)-(R)- and (+)-(S)-Lavandulol, (+)-Lavandulyl 2-methylbutanoate, and (+)-lavandulyl senecioate through orthoester johnson-claisen rearrangement

An efficient synthesis of (-)-(R)- and (+)-(S)-lavandulol, (+)-lavandulyl 2-methylbutanoate and (+)-lavandulyl senecioate is presented in this paper. The synthetic strategy features a chiral-pool approach to an allyl alcohol intermediate, and an orthoester Johnson-Claisen rearrangement as the key step. An efficient synthesis of (-)-(R)- and (+)-(S)-lavandulol, (+)-lavandulyl 2-methylbutanoate and (+)-lavandulyl senecioate is presented. The synthetic strategy features a chiral-pool approach to an allyl alcohol intermediate, and an orthoester Johnson-Claisen rearrangement as the key step. Copyright