58461-27-1

Basic information

• Product Name: (+/-)-LAVANDULOL
• Synonyms: 5-methyl-2-(1-methylethenyl)-4-hexen-1-o;5-methyl-2-(1-methylethenyl)-4-Hexen-1-ol;2-isopropenyl-5-methylhex-4-en-1-ol;4-Hexen-1-ol, 5-methyl-2-(1-methylethenyl)-;Einecs 261-264-2;rac-Lavandulol;5-Methyl-2-(prop-1-en-2-yl);hex-4-en-1-ol
• CAS NO: 58461-27-1
• Molecular Formula: C10H18O
• Molecular Weight: 154.24932
• EINECS: 261-264-2
• Product Categories: Aliphatics;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 58461-27-1.mol
• Article Data: 24

Chemical Properties

• Boiling Point: 230.2°Cat760mmHg
• Flash Point: 98 °C
• Appearance: /
• Density: 0.878 g/mL at 20 °C(lit.)
• Vapor Pressure: 0.0127mmHg at 25°C
• Refractive Index: n20/D 1.470
• Storage Temp.: 2-8°C
• PKA: 14.81±0.10(Predicted)
• CAS DataBase Reference: (+/-)-LAVANDULOL(CAS DataBase Reference)
• NIST Chemistry Reference: (+/-)-LAVANDULOL(58461-27-1)
• EPA Substance Registry System: (+/-)-LAVANDULOL(58461-27-1)

Safety Data

• Safety Statements: 23-24/25
• WGK Germany: 3
• F: 10-23
• Hazardous Substances Data: 58461-27-1(Hazardous Substances Data)

Usage

Description

(+/-)-LAVANDULOL is a chiral alcohol that occurs naturally in lavender oil. It is a mixture of two enantiomers, (R)and (S)-LAVANDULOL, which have distinct odors and properties. The (R)-enantiomer has a weak floral, herbal odor with a slightly lemon-like, fresh citrus fruity nuance, while the (S)-enantiomer has a very weak odor. The racemate, (+/-)-LAVANDULOL, has a weak floral, herbal odor.

Uses

Used in Fragrance Industry:
(+/-)-LAVANDULOL is used as a fragrance ingredient in the perfumery and cosmetics industry. The nature-identical (R)-enantiomer is preferred for its superior fragrance profile compared to the unnatural (S)-enantiomer and the racemate. It imparts a weak floral, herbal odor with a slightly lemon-like, fresh citrus fruity nuance, making it a valuable component in creating various scent profiles.

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

Upstream product

• 21634-63-9 methyl methyl-2-(1-methylethenyl)-2-hexenoate 
• 133872-76-1 Lavandulol tert-Butyldimethylsilyl Ether 
• 75950-55-9 1-(2,6-Dimethyl-hepta-1,5-diene-3-sulfonyl)-4-methyl-benzene 
• 541-47-9 3-Methylbutenoic acid 
• 497-67-6 2-(1-methylethenyl)-5-methyl-4-hexenoic acid 
• 21634-59-3 2-methyl-3-buten-2-yl 3-methyl-2-butenoate 
• 358-72-5 dimethylallyl diphosphate 
• 638-10-8 ethyl 3-methylbut-2-enoate 
• 129191-91-9 (E)-methyl γ-(benzothiazol-2-thio)-senecioate 
• 129191-92-0 (Z)-methyl γ-(benzothiazol-2-thio)-senecioate 
• 19041-17-9 methyl 4-bromo-3-methylbut-2-enoate 
• 924-50-5 Methyl 3,3-dimethylacrylate 
• 20886-47-9 N,3-dimethyl-N-phenylbut-2-enamide 
• 104543-27-3 2-isopropenyl-5-methyl-4-hexenal ethylene glycol acetal 

Downstream Products

• 1570098-90-6 C₃₃H₄₂O₄ 
• 25905-14-0 lavandulyl acetate 
• 23960-07-8 lavandulyl senecioate 
• 498-16-8 (R)-5-methyl-2-(prop-1-en-2-yl)hex-4-en-1-ol 
• 75697-98-2 2,6-dimethyl-3-formyl-1,5-heptadiene-lavandulal 
• 50373-53-0 (2S)-5-methyl-2-(prop-1-en-2-yl)hex-4-en-1-ol 
• 1063708-13-3 C₂₂H₂₇O₄P 
• 133872-85-2 3,5-Dinitro-benzoic acid 2-isopropenyl-5-methyl-4-oxo-hex-5-enyl ester 
• 881920-45-2 Succinic acid mono-((S)-2-isopropenyl-5-methyl-hex-4-enyl) ester 
• 20777-39-3 (-)-(R)-lavanduyl acetate 
• 144831-70-9 (2S)-5-methyl-2-(prop-1-en-2-yl)hex-4-enyl acetate 
• 79399-33-0 cis and trans-2,2-dimethyl-3-bromo-5-(1'-methyl-1'-phenylthioethyl)tetrahydropyran 

Relevant articles and documents

PROCESSES FOR PREPARING 2-ISOPROPENYL-5-METHYL-4-HEXENOIC ACID, 2-ISOPROPENYL-5-METHYL-4-HEXEN-1-OL, AND A CARBOXYLATE ESTER THEREOF

The present invention provides a process for preparing 2-isopropenyl-5-methyl-4-hexenoic acid of the following formula (4), comprising steps of: subjecting a Grignard reagent of the following general formula (1), wherein R1 represents a linear, branched, or aromatic monovalent hydrocarbon group having 1 to 8 carbon atoms, and X represents a chlorine atom, a bromine atom, or an iodine atom, and 1,1,1,3,3,3-hexamethyldisilazane to a deprotonation reaction to form a 1,1,1,3,3,3-hexamethyldisilazane derivative; and subjecting 2-methyl-3-buten-2-yl 3-methyl-2-butenoate of the following formula (3) to a rearrangement reaction in the presence of the 1, 1, 1,3,3,3-hexamethyldisilazane derivative to form 2-isopropenyl-5-methyl-4-hexenoic acid (4).

Chrysanthemyl diphosphate synthase operates in planta as a bifunctional enzyme with chrysanthemol synthase activity

Chrysanthemyl diphosphate synthase (CDS) is the first path-way-specific enzyme in the biosynthesis of pyrethrins, the most widely used plant-derived pesticide. CDS catalyzes c1′-2-3 cyclopropanation reactions of two molecules of dimethylallyl diphosphate (DMAPP) to yield chrysanthemyl diphosphate (CPP). Three proteins are known to catalyze this cyclopropanation reaction of terpene precursors. Two of them, phytoene and squalene synthase, are bifunctional enzymes with both prenyltransferase and terpene synthase activity. CDS, the other member, has been reported to perform only the prenyltransferase step. Here we show that the NDXXD catalytic motif of CDS, under the lower substrate conditions prevalent in plants, also catalyzes the next step, converting CPP into chrysanthemol by hydrolyzing the diphosphate moiety. The enzymatic hydrolysis reaction followed conventional Michaelis-Menten kinetics, with a Km value for CPP of 196 μM. For the chrysanthemol synthase activity, DMAPP competed with CPP as substrate. The DMAPP concentration required for half-maximal activity to produce chrysanthemol was ～100 μM, and significant substrate inhibition was observed at elevated DMAPP concentrations. The N-terminal peptide of CDS was identified as a plastid-targeting peptide. Transgenic tobacco plants overexpressing CDS emitted chrysanthemol at a rate of 0.12-0.16 μg h-1 g-1 fresh weight. We propose that CDS should be renamed a chrysanthemol synthase utilizing DMAPP as substrate.

A new synthesis of lavandulol via indium/palladium-mediated umpolung of vinyloxirane

A short synthesis of lavandulol is achieved by the In/Pd-mediated reaction of isopropenyloxirane with 3-methylbut-2-enal.