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3681-71-8

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  • 100% Safe Customs Clearance Faithful Supply raw material cis-3-Hexenyl Acetate/ 99% cis-3-Hexenyl Acetate liquid/ pure cis-3-Hexenyl Acetate/ raw Leaf acetate

    Cas No: 3681-71-8

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3681-71-8 Usage

Description

cis-3-Hexen-1 -y 1-acetate has a powerful green, floral note reminiscent of banana. It may be prepared by acetylation of the corresponding alcohol.

Chemical Properties

Different sources of media describe the Chemical Properties of 3681-71-8 differently. You can refer to the following data:
1. cis-3-Hexen-1-yl acetate has a powerful, green, fruity, floral note reminiscent of banana.
2. Colorless liquid
3. (Z)-3-Hexenyl Acetate has been identified in many fruit aromas and green tea. It is a prototype for green odors and is often used in combination with (Z)-3-hexenol.

Occurrence

Reported found in apple, bilberry, guava, strawberry, black and green tea, yellow and purple passion fruit, citrus peel oils, melon, peach, raspberry, pear, pineapple, melon, celery, tomato, corn mint oil, spearmint oil, brandies, grape wines, soybeans, olive, plum, plumcot, starfruit, mango, cauliflower, dill, lovage, corn oil, nectarines, Chinese quince and chamomile oil.

Preparation

By acetylation of the corresponding alcohol

Definition

ChEBI: An acetate ester that results from the formal condensation of acetic acid with (Z)-hex-3-en-1-ol.

Taste threshold values

Taste characteristics at 10 ppm: green, fruity, apple and pear with fresh tropical nuances

Synthesis Reference(s)

Canadian Journal of Chemistry, 65, p. 2327, 1987 DOI: 10.1139/v87-388

Flammability and Explosibility

Flammable

Check Digit Verification of cas no

The CAS Registry Mumber 3681-71-8 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 3,6,8 and 1 respectively; the second part has 2 digits, 7 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 3681-71:
(6*3)+(5*6)+(4*8)+(3*1)+(2*7)+(1*1)=98
98 % 10 = 8
So 3681-71-8 is a valid CAS Registry Number.
InChI:InChI=1/C8H14O2/c1-3-4-5-6-7-10-8(2)9/h4-5H,3,6-7H2,1-2H3/b5-4-

3681-71-8 Well-known Company Product Price

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  • Alfa Aesar

  • (A19380)  cis-3-Hexenyl acetate, 99%   

  • 3681-71-8

  • 25g

  • 597.0CNY

  • Detail
  • Alfa Aesar

  • (A19380)  cis-3-Hexenyl acetate, 99%   

  • 3681-71-8

  • 100g

  • 1167.0CNY

  • Detail

3681-71-8SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 11, 2017

Revision Date: Aug 11, 2017

1.Identification

1.1 GHS Product identifier

Product name (3Z)-hex-3-en-1-yl acetate

1.2 Other means of identification

Product number -
Other names Leaf Acetate

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Fragrances
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:3681-71-8 SDS

3681-71-8Synthetic route

(Z)-3-Hexen-1-ol
928-96-1

(Z)-3-Hexen-1-ol

acetic anhydride
108-24-7

acetic anhydride

(Z)-3-Hexenyl acetate
3681-71-8

(Z)-3-Hexenyl acetate

Conditions
ConditionsYield
zinc(II) perchlorate at 20℃; for 1.83333h;99%
(Z)-3-Hexen-1-ol
928-96-1

(Z)-3-Hexen-1-ol

acetic acid
64-19-7

acetic acid

(Z)-3-Hexenyl acetate
3681-71-8

(Z)-3-Hexenyl acetate

Conditions
ConditionsYield
With cobalt(II) chloride at 60℃; for 10h;97%
(Z)-3-Hexen-1-ol
928-96-1

(Z)-3-Hexen-1-ol

acetyl chloride
75-36-5

acetyl chloride

(Z)-3-Hexenyl acetate
3681-71-8

(Z)-3-Hexenyl acetate

Conditions
ConditionsYield
With N,N-dimethyl-aniline In diethyl ether for 2h; Heating;90%
vinyl acetate
108-05-4

vinyl acetate

(Z)-3-Hexen-1-ol
928-96-1

(Z)-3-Hexen-1-ol

(Z)-3-Hexenyl acetate
3681-71-8

(Z)-3-Hexenyl acetate

Conditions
ConditionsYield
With rape seedlings lipase In hexane at 40℃; for 48h; Reagent/catalyst; Solvent; Molecular sieve; Green chemistry; Enzymatic reaction;70.3%
With rape seed lipase In hexane at 40℃; for 24h; Enzymatic reaction;
(Z)-3-Hexen-1-ol
928-96-1

(Z)-3-Hexen-1-ol

ethylene glycol diacetate
111-55-7

ethylene glycol diacetate

(Z)-3-Hexenyl acetate
3681-71-8

(Z)-3-Hexenyl acetate

Conditions
ConditionsYield
With Candida antarctica lipase B immobilized on a macroporous acrylic resin at 40℃; for 19h; Temperature; Green chemistry; Enzymatic reaction;70%
(Z)-3-Hexen-1-ol
928-96-1

(Z)-3-Hexen-1-ol

sodium acetate
127-09-3

sodium acetate

acetic anhydride
108-24-7

acetic anhydride

(Z)-3-Hexenyl acetate
3681-71-8

(Z)-3-Hexenyl acetate

2-(3-ethyloxiranyl)ethyl acetate
113816-35-6

2-(3-ethyloxiranyl)ethyl acetate

A

(Z)-3-Hexenyl acetate
3681-71-8

(Z)-3-Hexenyl acetate

B

acetic acid hex-3-enyl ester
3681-82-1

acetic acid hex-3-enyl ester

Conditions
ConditionsYield
With 2-(N,N-dimethylamino)ethanol; samarium diiodide In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide for 2.5h; Ambient temperature; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
2,4-hexadien-1-ol acetate
1516-17-2

2,4-hexadien-1-ol acetate

(Z)-3-Hexenyl acetate
3681-71-8

(Z)-3-Hexenyl acetate

Conditions
ConditionsYield
With hydrogen; [Ru(C5Me5)(1,3-COD)]BF4 In acetone at 70℃; under 3750.38 Torr; Product distribution / selectivity;
With hydrogen; 2-methoxy-phenol; [Ru(C5Me5)(1,3-COD)]BF4 In acetone at 70℃; under 3750.38 Torr; Product distribution / selectivity;
With hydrogen; maleic acid; [Ru(C5Me5)(1,3-COD)]BF4 In acetone at 70℃; under 3750.38 Torr; Product distribution / selectivity;
3-hexynyl acetate

3-hexynyl acetate

(Z)-3-Hexenyl acetate
3681-71-8

(Z)-3-Hexenyl acetate

Conditions
ConditionsYield
With hydrogen; tetrabutylammonium borohydride In tetrahydrofuran; N,N-dimethyl-formamide at 30℃; under 6080.41 Torr; Autoclave; diastereoselective reaction;99.6 %Chromat.
(Z)-3-Hexen-1-ol
928-96-1

(Z)-3-Hexen-1-ol

ethyl acetate
141-78-6

ethyl acetate

(Z)-3-Hexenyl acetate
3681-71-8

(Z)-3-Hexenyl acetate

Conditions
ConditionsYield
at 88℃; under 760.051 Torr; for 2h; Catalytic behavior; Reagent/catalyst;
(3Z)-hexenal
6789-80-6

(3Z)-hexenal

(Z)-3-Hexenyl acetate
3681-71-8

(Z)-3-Hexenyl acetate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: aldehyde reductase; nicotinamide adenine dinucleotide phosphate / Enzymatic reaction
2: BAHD acyltransferase / Enzymatic reaction
View Scheme
(Z)-3-Hexen-1-ol
928-96-1

(Z)-3-Hexen-1-ol

acetylcoenzyme A
72-89-9

acetylcoenzyme A

(Z)-3-Hexenyl acetate
3681-71-8

(Z)-3-Hexenyl acetate

Conditions
ConditionsYield
With BAHD acyltransferase Enzymatic reaction;
(Z)-3-Hexenyl acetate
3681-71-8

(Z)-3-Hexenyl acetate

N-(2-ethyltetrahydrofuran-3-yl)acetamide

N-(2-ethyltetrahydrofuran-3-yl)acetamide

Conditions
ConditionsYield
With bis{rhodium[3,3'-(1,3-phenylene)bis(2,2-dimethylpropanoic acid)]}; O-(2,4-dinitrophenyl)hydroxylamine In 2,2,2-trifluoroethanol at 20℃; for 51h; Inert atmosphere;61%
(Z)-3-Hexenyl acetate
3681-71-8

(Z)-3-Hexenyl acetate

Acetic acid 2-((2S,3R)-3-ethyl-oxiranyl)-ethyl ester

Acetic acid 2-((2S,3R)-3-ethyl-oxiranyl)-ethyl ester

Conditions
ConditionsYield
With perfluoro-cis-2-n-butyl-3-n-propyloxaziridine In chloroform at -60℃; for 0.333333h;85%
formaldehyd
50-00-0

formaldehyd

(Z)-3-Hexenyl acetate
3681-71-8

(Z)-3-Hexenyl acetate

Acetic acid (E)-3-hydroxymethyl-hex-4-enyl ester
84143-43-1

Acetic acid (E)-3-hydroxymethyl-hex-4-enyl ester

Conditions
ConditionsYield
With ethylaluminum dichloride In n-heptane; dichloromethane at 0℃; for 1h;59%
(Z)-3-Hexenyl acetate
3681-71-8

(Z)-3-Hexenyl acetate

Acetic acid 3,4-difluoro-hexyl ester
103239-64-1

Acetic acid 3,4-difluoro-hexyl ester

Conditions
ConditionsYield
With fluorine In ethanol; chloroform at -75℃;50%
2-naphthaloyl chloride

2-naphthaloyl chloride

cis 3-hexen-1-yl 3-(β-naphthyl)-3-oxo-propionate
203174-60-1

cis 3-hexen-1-yl 3-(β-naphthyl)-3-oxo-propionate

Conditions
ConditionsYield
With lithium diisopropyl amide In tetrahydrofuran; water
(Z)-3-Hexenyl acetate
3681-71-8

(Z)-3-Hexenyl acetate

C8H15NO2

C8H15NO2

Conditions
ConditionsYield
With bis{rhodium[3,3'-(1,3-phenylene)bis(2,2-dimethylpropanoic acid)]}; O-(2,4-dinitrophenyl)hydroxylamine In 2,2,2-trifluoroethanol at 50℃; for 51h;61%
(Z)-3-Hexenyl acetate
3681-71-8

(Z)-3-Hexenyl acetate

carbon monoxide
201230-82-2

carbon monoxide

3,5-dimethyl(diacetoxy-λ3-iodanyl)benzene
680980-39-6

3,5-dimethyl(diacetoxy-λ3-iodanyl)benzene

C11H18O6

C11H18O6

C11H18O6

C11H18O6

Conditions
ConditionsYield
With palladium diacetate; trifluoroborane diethyl ether In toluene; acetonitrile at 20℃; under 760.051 Torr; for 24h; Schlenk technique; Overall yield = 91 %; Overall yield = 47.3 mg; diastereoselective reaction;

3681-71-8Relevant articles and documents

Scalable green approach toward fragrant acetates

Puchl'Ová, Eva,Szolcsányi, Peter

supporting information, (2020/08/07)

The advantageous properties of ethylene glycol diacetate (EGDA) qualify it as a useful substitute for glycerol triacetate (GTA) for various green applications. We scrutinised the lipase-mediated acetylation of structurally diverse alcohols in neat EGDA furnishing the range of naturally occurring fragrant acetates. We found that such enzymatic system exhibits high reactivity and selectivity towards activated (homo) allylic and non-activated primary/secondary alcohols. This feature was utilised in the scalable multigram synthesis of fragrant (Z)-hex-3-en-1-yl acetate in 70percent yield. In addition, the Lipozyme 435/EGDA system was also found to be applicable for the chemo-selective acetylation of (hydroxyalkyl) phenols as well as for the kinetic resolution of chiral secondary alcohols. Lastly, its discrimination power was demonstrated in competitive experiments of equimolar mixtures of two isomeric alcohols. This enabled the practical synthesis of 1-pentyl acetate isolated as a single product in 68percent yield from the equimolar mixture of 1-pentanol and 3-pentanol.

Identification of (Z)-3:(E)-2-Hexenal isomerases essential to the production of the leaf aldehyde in plants

Kunishima, Mikiko,Yamauchi, Yasuo,Mizutani, Masaharu,Kuse, Masaki,Takikawa, Hirosato,Sugimoto, Yukihiro

, p. 14023 - 14033 (2016/07/11)

The green odor of plants is characterized by green leaf volatiles (GLVs) composed of C6 compounds. GLVs are biosynthesized from polyunsaturated fatty acids in thylakoid membranes by a series of enzymes. A representative member of GLVs (E)-2-hexenal, known as the leaf aldehyde, has been assumed to be produced by isomerization from (Z)-3-hexenal in the biosynthesis pathway; however, the enzyme has not yet been identified. In this study, we purified the (Z)-3:(E)-2-hexenal isomerase (HI) from paprika fruits and showed that various plant species have homologous HIs. Purified HI is a homotrimeric protein of 110 kDa composed of 35-kDa subunits and shows high activity at acidic and neutral pH values. Phylogenetic analysis showed that HIs belong to the cupin superfamily, and at least three catalytic amino acids (His, Lys, Tyr) are conserved in HIs of various plant species. Enzymatic isomerization of (Z)-3-hexenal in the presence of deuterium oxide resulted in the introduction of deuterium at the C4 position of (E)-2-hexenal, and a suicide substrate 3-hexyn-1-al inhibited HI irreversibly, suggesting that the catalytic mode of HI is a keto-enol tautomerism reaction mode mediated by a catalytic His residue. The gene expression of HIs in Solanaceae plants was enhanced in specific developmental stages and by wounding treatment. Transgenic tomato plants overexpressing paprika HI accumulated (E)-2-hexenal in contrast to wild-type tomato plants mainly accumulating (Z)-3-hexenal, suggesting that HI plays a key role in the production of (E)-2-hexenal in planta.

Effective synthesis of cis-3-hexen-1-yl acetate via transesterification over KOH/γ-Al2O3: Structure and catalytic performance

Li, Xiaoshuan,Yu, Dinghua,Zhang, Wengui,Li, Zhengwen,Zhang, Xiaowei,Huang, He

, p. 1 - 7 (2013/06/04)

Cis-3-hexen-1-yl acetate is a significant green note flavor compound and widely used in the food and cosmetic industry. In this research, a series of solid base KOH/γ-Al2O3 have been prepared and been utilized for the synthesis of cis-3-hexen-1-yl acetate via transesterification from cis-3-hexen-1-yl and ethyl acetate. The catalysts were also characterized by several physic-chemical techniques such as X-ray diffraction (XRD), Fourier transform infrared (FT-IR) spectroscopy, N2 adsorption, CO 2-temperature-programmed desorption (CO2-TPD), and X-ray fluorescence (XRF). 30%KOH/Al2O3 was suggested to be the best conversion due to the cis-3-hexen-1-ol conversion of 59.3% at a temperature 88 °C within 2 h. Characterization results showed that KOH transformed into Al-O-K and K2O·CO2 species during the calcination process. It was confirmed that K2O·CO2 disappeared and Al-O-K groups existed on the surface of the water-washing 30%KOH/Al 2O3 which was inactive for transesterification. K 2O·CO2 species might be the major active species on KOH/Al2O3, and Al-O-K groups was inactive for cis-3-hexen-yl acetate synthesis.

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