153665-39-5

Usage

Uses

Used in Perfumery Industry:
2-Hepten-4-ol,6-methyl-, (2E,4S)is used as a fragrance ingredient for its floral and citrus-like scent, contributing to the creation of various perfumes and other scented products.
Used in Personal Care Industry:
In the personal care industry, 2-Hepten-4-ol,6-methyl-, (2E,4S)is used as an antimicrobial agent in the production of deodorants and antiperspirants, helping to control odor and perspiration.
Used in Food Industry:
2-Hepten-4-ol,6-methyl-, (2E,4S)is utilized as a flavoring agent in food products, enhancing the taste and aroma of various culinary offerings.

Synthetic route

(4S)-6-methylhept-2-yn-4-ol (60018-72-6) → (S,E)-6-Methyl-3-hepten-4-ol (153665-39-5)

Conditions	Yield
With lithium aluminium tetrahydride In tetrahydrofuran for 14h; Heating;	61%
With ammonia; sodium

6-methyl-2-(cis)-hepten-4(R)-ol (109214-86-0) → (4R)-(2E)-6-methyl-2-hepten-4-ol (66900-48-9) + (S,E)-6-Methyl-3-hepten-4-ol (153665-39-5)

Conditions	Yield
With L-(+)-diisopropyl tartrate

(E)-6-methylhept-2-en-4-one (23769-10-0) → (4R)-(2E)-6-methyl-2-hepten-4-ol (66900-48-9) + (S,E)-6-Methyl-3-hepten-4-ol (153665-39-5)

Conditions	Yield
With (R,R)-RuCl2(2,2'-bis(di-3,5-xylylphosphino)-1,1'-binaphthyl)(1,1-dianisyl-2-isopropyl-1,2-ethylenediamine); hydrogen; potassium carbonate In isopropyl alcohol at 28 - 30℃; under 7600 Torr; for 37h; Yield given; Yields of byproduct given. Title compound not separated from byproducts;

trans-Crotonaldehyde (123-73-9) + isobutylmagnesium bromide (926-62-5) → (4R)-(2E)-6-methyl-2-hepten-4-ol (66900-48-9) + (S,E)-6-Methyl-3-hepten-4-ol (153665-39-5)

Conditions	Yield
Stage #1: trans-Crotonaldehyde; isobutylmagnesium bromide In diethyl ether Grignard reaction; Stage #2: With titanium(IV) isopropylate; tert.-butylhydroperoxide; diethyl (2S,3S)-tartrate In dichloromethane at -20℃; Epoxidation; resolution of racemate; Title compound not separated from byproducts;

(+/-)-6-methyl-2-heptyn-4-ol (59983-72-1) → (S,E)-6-Methyl-3-hepten-4-ol (153665-39-5)

Conditions	Yield
Multi-step reaction with 3 steps 1: 92 percent / pyridine 2: KOH / methanol / 3 h / Ambient temperature 3: 61 percent / LiAlH4 / tetrahydrofuran / 14 h / Heating View Scheme
Multi-step reaction with 3 steps 1: 94 percent / pyridine / 14 h / Ambient temperature 2: H2O; methanol / 7.2 h / Ambient temperature; Lipase OF (Meito OF 360), phosphate buffer, pH=7.5 3: 61 percent / LiAlH4 / tetrahydrofuran / 14 h / Heating View Scheme
Multi-step reaction with 3 steps 1: Py 2: aq. NaOH 3: Na, liq. NH3 View Scheme

(+/-)-1-(2'-methylpropyl)-2-butynyl acetate (70063-89-7) → (S,E)-6-Methyl-3-hepten-4-ol (153665-39-5)

Conditions	Yield
Multi-step reaction with 4 steps 1: 40 percent / H2O; methanol / 15 h / 20 °C / Lipase A (Amano), phosphate buffer, pH=7.5 2: 94 percent / pyridine / 14 h / Ambient temperature 3: H2O; methanol / 7.2 h / Ambient temperature; Lipase OF (Meito OF 360), phosphate buffer, pH=7.5 4: 61 percent / LiAlH4 / tetrahydrofuran / 14 h / Heating View Scheme
Multi-step reaction with 2 steps 1: KOH / methanol / 3 h / Ambient temperature 2: 61 percent / LiAlH4 / tetrahydrofuran / 14 h / Heating View Scheme

(+/-)-1-(2'-methylpropyl)-2-butynyl propanoate (143446-87-1) → (S,E)-6-Methyl-3-hepten-4-ol (153665-39-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: H2O; methanol / 7.2 h / Ambient temperature; Lipase OF (Meito OF 360), phosphate buffer, pH=7.5 2: 61 percent / LiAlH4 / tetrahydrofuran / 14 h / Heating View Scheme

(S)-1-(2-methylpropyl)-2-butynyl 3,5-dinitrobenzoate (143446-88-2) → (S,E)-6-Methyl-3-hepten-4-ol (153665-39-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: 68 percent / K2CO3 / CH2Cl2; methanol / 14 h / Ambient temperature 2: 61 percent / LiAlH4 / tetrahydrofuran / 14 h / Heating View Scheme

phthalic acid mono-((S)-1-isobutyl-but-2-ynyl) ester (60018-73-7) → (S,E)-6-Methyl-3-hepten-4-ol (153665-39-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: aq. NaOH 2: Na, liq. NH3 View Scheme

isovaleraldehyde (590-86-3) → (S,E)-6-Methyl-3-hepten-4-ol (153665-39-5)

Conditions	Yield
Multi-step reaction with 4 steps 1: (i) EtMgBr, (ii) /BRN= 773692/ 2: Py 3: aq. NaOH 4: Na, liq. NH3 View Scheme

N,N-dimethylacetamide dimethyl acetal (18871-66-4) + (S,E)-6-Methyl-3-hepten-4-ol (153665-39-5) → (E)-(S)-3,7-Dimethyl-oct-4-enoic acid dimethylamide (59983-67-4)

Conditions	Yield
In xylene Heating;

Triethyl orthoacetate (78-39-7) + (S,E)-6-Methyl-3-hepten-4-ol (153665-39-5) → (E)-(S)-3,7-Dimethyl-oct-4-enoic acid ethyl ester (59983-66-3)

Conditions	Yield
With propionic acid

(S,E)-6-Methyl-3-hepten-4-ol (153665-39-5) + ethyl vinyl ether (109-92-2) → (S)-6-methyl-4-vinyloxy-hept-2t-ene (59983-80-1)

Conditions	Yield
With mercury(II) diacetate

N,N-diisopropylcarbamoyl chloride (19009-39-3) + (S,E)-6-Methyl-3-hepten-4-ol (153665-39-5) → Diisopropyl-carbamic acid (E)-(S)-1-isobutyl-but-2-enyl ester (100297-24-3)

(S,E)-6-Methyl-3-hepten-4-ol (153665-39-5) → (S)-2-methyl-4-heptanol (93031-25-5) + (R)-2-methyl-4-heptanol (93031-21-1)

Conditions	Yield
With hydrogen; platinum on activated charcoal In methanol at 20℃; Catalytic hydrogenation; Title compound not separated from byproducts;

(S,E)-6-Methyl-3-hepten-4-ol (153665-39-5) → (+)(R)-2.6-dimethyl-octanoic acid-(8)-ethyl ester (59983-82-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: EtCO2H 2: H2 / Pd-C / ethanol View Scheme

(S,E)-6-Methyl-3-hepten-4-ol (153665-39-5) → (R)-3,7-dimethyloctanoic acid (32531-52-5)

Conditions	Yield
Multi-step reaction with 3 steps 1: EtCO2H 2: aq. NaOH / methanol 3: H2 / Raney-Ni View Scheme
Multi-step reaction with 3 steps 1: xylene / Heating 2: KOH / ethane-1,2-diol; H2O / 200 °C 3: H2 / Raney-Ni View Scheme

(S,E)-6-Methyl-3-hepten-4-ol (153665-39-5) → 3(R),7-dimethyl octanoic acid dimethylamide (59983-83-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: xylene / Heating 2: H2 / Pd-C / methanol View Scheme

(S,E)-6-Methyl-3-hepten-4-ol (153665-39-5) → 3(S)7-dimethyl-4(trans)-octenoic acid (59983-64-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: EtCO2H 2: aq. NaOH / methanol View Scheme
Multi-step reaction with 2 steps 1: xylene / Heating 2: KOH / ethane-1,2-diol; H2O / 200 °C View Scheme

Upstream product

• 60018-72-6 (4S)-6-methylhept-2-yn-4-ol 
• 109214-86-0 6-methyl-2-(cis)-hepten-4(R)-ol 
• 23769-10-0 (E)-6-methylhept-2-en-4-one 
• 123-73-9 trans-Crotonaldehyde 
• 926-62-5 isobutylmagnesium bromide 
• 59983-72-1 (+/-)-6-methylhept-5-yn-4-ol 
• 70063-89-7 (+/-)-1-(2'-methylpropyl)-2-butynyl acetate 
• 143446-87-1 (+/-)-1-(2'-methylpropyl)-2-butynyl propanoate 
• 143446-88-2 (S)-1-(2-methylpropyl)-2-butynyl 3,5-dinitrobenzoate 
• 60018-73-7 phthalic acid mono-((S)-1-isobutyl-but-2-ynyl) ester 
• 590-86-3 isovaleraldehyde 

Relevant academic research and scientific papers

Aggregation pheromones and host kairomones of West Indian sugarcane weevil, Metamasius hemipterus sericeus

Coupled gas chromatographic-electroantennographic detection (GC-EAD) analyses and coupled GC-mass spectrometry (MS) of volatiles produced by male and female West Indian sugarcane weevils (WISW), Metamasius hemipterus sericeus (Oliv.), revealed eight male specific, EAD-active compounds: 3-pentanol (1), 2-methyl-4-heptanol (2), 2-methyl-4-octanol (3) 4-methyl-5-nonanol (4), and the corresponding ketones. In field experiments in Florida, alcohols 1-4 in combination with sugarcane were most attractive, whereas addition of the ketones or replacement of alcohols with ketones significantly reduced attraction. In Costa Rica field experiments testing alcohols 1-4 singly and in all binary, ternary, and quaternary combinations revealed 4 in combination with 2 was the major aggregation pheromone, equally attracting male and female WISW. Stereoisomeric 4 and (4S,5S)-4, the only isomer produced by WISW, were equally attractive. Addition of 4S-, 4R- or (±)-2 to (4S,5S)-4 significantly enhanced attraction Sugarcane stalks in combination with 2 plus 4 (ratio of 1:8) were highly synergistic, whereas EAD-active sugarcane volatiles ethyl acetate, ethyl propionate, or ethyl butyrate only moderately increased attractiveness of the pheromone lure.

Pheromone Synthesis, CXLV. Synthesis of the Enantiomers of Rhynchophorol , the Male-Produced Aggregation Pheromone of the American Palm Weevil, Rhynchophorus palmarum

Both the enantiomers of rhynchophorol , the male-produced aggregation pheromone of the American palm weevil (Rhynchophorus palmarum), have been synthesized by reducing their precursors, (R)- and (S)-6-methyl-2-heptyn-4-ol (2), which have been prepared by lipase-mediated asymmetric hydrolysis of the corresponding acetate and propionate.Key Words: American palm weevil / Lipases / Pheromones / Rhynchophorol Rhynchophorus palmarum / Enzymes