58461-27-1

Usage

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

• 50-00-0 formaldehyd 
• 110-93-0 6-Methyl-hept-5-en-2-on 
• 67986-78-1 N,5-dimethyl-N-phenyl-2-isopropenyl-4-hexenamide 
• 5617-92-5 chrysanthemol 
• 110-88-3 1,3,5-Trioxan 
• 6090-15-9 2,6-dimethylhept-5-en-2-ol 
• 115-18-4 2-methyl-3-buten-2-ol 
• 26902-25-0 3-methyl-1-(3-methylbut-2-enyloxy)but-2-ene 
• 91914-58-8 isopropenyl-2 methyl-5 hexene-4 thioate de S-methyle 
• 25905-14-0 lavandulyl acetate 
• 3304-29-8 5-Methyl-2-(1'-methylethyliden)-4-hexensaeure-ethylester 
• 79499-67-5 2,6-Dimethyl-3-(phenylthio)-1,5-heptadiene 
• 70473-50-6 2-(phenylthio)-3-methyl-3-buten-1-ol 
• 870-63-3 prenyl bromide 

Downstream Products

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

Relevant academic research and scientific papers

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).

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.

Biomimetic total synthesis of (±)-doitunggarcinone A and (+)-garcibracteatone

A full account of our oxidative radical cyclization approach to the synthesis of garcibracteatone and doitunggarcinone A is presented. This includes the first enantioselective synthesis of garcibracteatone, which allowed the absolute configuration of the natural compound to be determined. The first synthesis of doitunggarcinone A is also described, which confirms our reassignment of the relative configuration of this molecule. Novel syntheses of monoterpene fragments used to construct the target molecules are also reported.

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.

Synthesis of 6-(poly)prenyl-substituted polyprenols and their phosphates

The 6-(poly)prenyl-substituted polyprenols 7, 9, 11, and 13 were synthesized: (1) 7 from 2-geranyl-farnesal and methyl 4-bromo-3-methyl-2- butenoate, (2) 9 from 2-prenyl-geranyl bromide and ethyl acetoacetate, via ketone 29, (3) 11 from ethyl acetoacetate, geranyl bromide, and (E)-1-t- butyldiphenylsiloxy-5-iodo-3-methyl-2-pentene, via β-keto ester 35, and (4) 13 from geraniol by acid catalyzed condensation. These highly branched polyprenols 7, 9, 11, and 13 were transformed into the corresponding disodium phosphates 8, 10, 12, and 14, respectively.

A synthesis of (±)-lavandulol using a silyl-to-hydroxy conversion in the presence of 1,1-disubstituted and trisubstituted double bonds

Silylcuprates and silylzincates react with α,β-unsaturated aldehydes, esters, ketones and amides 19 unsubstituted at the β-position in higher yield if trimethylsilyl chloride is present. Applying this method, conjugate addition of the silylcuprate 26 derived from (Z)-chloro(2-methylbut-2-enyl)diphenylsilane 24, itself prepared by an improved route, to 3-methylene-6-methylhept-5-en-2-one 25 gave 3-[(Z)-2-methylbut-2-enyl(diphenyl)silyl]methyl-6-methylhept-5-en-2-one 27. A Wittig reaction gave 3-[(Z)-2-methylbut-2-enyl(diphenyl)silyl]methyl-2,6-dimethylhepta-1,5-diene 28 and silyl-to-hydroxy conversion gave lavandulol 1, even in the presence of the 1,1-disubstituted and trisubstituted double bonds. The hydroxy group of the 3-hydroxysilane, 2,6-dimethyl-3-{[(Z)-2-methylbut-2-enyl]diphenylsilyl}methylhept-5-en-2-ol 30, activated the allylsilane group towards protodesilylation. Chloro(diphenyl)methallylsilane 35 is easier to make than the chloride 24, and should be an alternative allylsilane that can make a lithium and hence a cuprate reagent like 26.

Conjugate addition of silyl groups to β-unsubstituted enones, and Si-to-OH conversion: A synthesis of (±)-lavandulol

TMS chloride raises the yield in the conjugate addition of silylcuprates and zincates to β-unsubstituted enones, and Si-to-OH conversion is possible using the 2-methylbut-2-enyl(diphenyl)silyl group in the presence of highly nucleophilic alkenes. Both reactions are used in a synthesis of lavandulol.

Enantio- and diastereoselective protonation of photodienols: Total synthesis of (R)-(-)-lavandulol

The total synthesis of (R)-(-)-lavandulol 1 has been achieved by asymmetric protonation of photodienols obtained from the irradiation of prochiral α,β-unsaturated esters. The photodeconjugation of ethyl 5-methyl-2-(1'-methylethylidene)-4-hexenoate (3a), carried out in the presence of catalytic amounts of a β-amino alcohol prepared from (±)-camphor, gives the β,γ-unsaturated isomer 2a in good yields but with moderate enantioselectivities (40% ee). In contrast, irradiation of the corresponding ester 3b, bearing the 1,2:5,6-di-O-isopropylidene-D-glucose group as a chiral alkoxy moiety, affords the deconjugated product 2b in high de (> 95%). Simple reduction of the ester function with LiAlH4 gives (R)-(-)-lavandulol (1) without loss of optical purity.