2305-25-1

Basic information

• Product Name: ETHYL 3-HYDROXYHEXANOATE
• Synonyms: ETHYL 3 HYDROXY CAPROATE;(+/-)-ETHYL 3-HYDROXYHEXANOATE;ETHYL 3-HYDROXYHEXANOATE;FEMA 3545;3-hydroxy-hexanoicaciethylester;Hexanoic acid, 3-hydroxy-, ethyl ester;Hexanoicacid,3-hydroxy-,ethylester;Ethyl 3-hydroxybhexanoate
• CAS NO: 2305-25-1
• Molecular Formula: C₈H₁₆O₃
• Molecular Weight: 160.21
• EINECS: 218-973-7
• Product Categories: Pharmaceutical Intermediates;Alphabetical Listings;E-F;Flavors and Fragrances
• Mol File: 2305-25-1.mol

Chemical Properties

• Boiling Point: 90-92 °C14 mm Hg(lit.)
• Flash Point: 202 °F
• Appearance: /
• Density: 0.974 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.00608mmHg at 25°C
• Refractive Index: n20/D 1.428(lit.)
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 14.45±0.20(Predicted)
• CAS DataBase Reference: ETHYL 3-HYDROXYHEXANOATE(CAS DataBase Reference)
• NIST Chemistry Reference: ETHYL 3-HYDROXYHEXANOATE(2305-25-1)
• EPA Substance Registry System: ETHYL 3-HYDROXYHEXANOATE(2305-25-1)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 3
• TSCA: Yes
• Hazardous Substances Data: 2305-25-1(Hazardous Substances Data)

Usage

Uses

Used in Flavor and Fragrance Industry:
ETHYL 3-HYDROXYHEXANOATE is used as a flavoring agent for its sweet, fruity, and grape-like taste with citrus notes, particularly at a concentration of 80 ppm. It is commonly found in the natural aroma of fruits like guava, bananas, and citrus fruits.
Used in Beverage Industry:
ETHYL 3-HYDROXYHEXANOATE is used as a flavor enhancer in the production of beverages such as cognac, Scotch whiskey, red and white wine, and fruit juices like orange, grapefruit, and tangerine juice. It helps to create a more complex and appealing taste profile in these drinks.
Used in Food Industry:
ETHYL 3-HYDROXYHEXANOATE is used as an additive in the food industry to impart a sweet, fruity, and citrusy flavor to various products. It can be found in the natural composition of fruits like pineapple, strawberry, passion fruit, mango, quince, wood apple, mountain papaya, pawpaw, and hog plum (Spondias mombins L.).
Used in Perfumery:
ETHYL 3-HYDROXYHEXANOATE is used as a fragrance ingredient in the perfumery industry due to its fruity odor, which can add depth and complexity to various scent compositions.

Synthesis Reference(s)

The Journal of Organic Chemistry, 39, p. 269, 1974 DOI: 10.1021/jo00916a043

InChI:InChI=1/C8H16O3/c1-3-5-7(9)6-8(10)11-4-2/h7,9H,3-6H2,1-2H3/t7-/m0/s1

Upstream product

• 3249-68-1 ethyl butyroyl acetate 
• 112083-63-3 ethyl (-)-(2S)-oxirane-2-acetate 
• 112100-39-7 (S)-4-iodo-3-hydroxy-butyric acid ethyl ester 
• 16205-90-6 ethyl 2-hexynoate 
• 1373154-19-8 ethyl (Z)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)hex-2-enoate 
• 1252813-46-9 (R)-ethyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)hexanoate 
• 130158-22-4 ethyl (S)-3-((tert-butyldimethylsilyl)oxy)-4-iodobutanoate 
• 123731-68-0 (S)-1,2-epoxypentane 
• 41014-93-1 2-(S)-hydroxyvaleric acid 
• 6600-40-4 L-Norvaline 
• 29117-54-2 (S)-(-)-1,2-pentanediol 
• 6728-26-3 (E)-2-Hexenal 
• 64-17-5 ethanol 
• 66997-60-2 (+)-(3S)-3-hydroxyhexanoic acid 

Downstream Products

• 123731-62-4 (+/-)-(E)-1-(2-bromo-3,4,5-trimethoxyphenyl)-1-hepten-4-ol 
• 30263-96-8 (2S,3R)-5-Propyl-2-(3,4,5-trimethoxy-phenyl)-tetrahydro-furan-3-ol 
• 123731-55-5 Toluene-4-sulfonic acid 3-(tert-butyl-dimethyl-silanyloxy)-hexyl ester 
• 28890-33-7 (2S,3aS,9bS)-6-Hydroxy-7,8-dimethoxy-2-propyl-2,3,3a,9b-tetrahydro-furo[3,2-c]isochromen-5-one 
• 28890-33-7 monocerin 
• 28890-33-7 (+/-)-monocerin 
• 28890-33-7 (2R,3aR,9bR)-2,3,3a,9b-tetrahydro-6-hydroxy-7,8-dimethoxy-2-propyl-5H-furo(3,2-c)(2)benzopyran-5-one 
• 123731-63-5 2-(2-bromo-3,4,5-trimethoxyphenyl)-5-propyltetrahydrofuran-3-ol 
• 123731-65-7 6-((2S,3R)-3-Hydroxy-5-propyl-tetrahydro-furan-2-yl)-2,3,4-trimethoxy-benzoic acid 
• 123731-61-3 (+/-)-2-bromo-1-<(E)-4-t-butyldimethylsilyloxy-1-heptenyl>-3,4,5-trimethoxybenzene 
• 123731-59-9 1-(2-bromo-3,4,5-trimethoxyphenyl)-4-t-butyldimethylsilyloxy-1-heptanol 
• 123731-58-8 Acetic acid 1-(2-bromo-3,4,5-trimethoxy-phenyl)-4-(tert-butyl-dimethyl-silanyloxy)-heptyl ester 
• 123731-57-7 1-(4-t-butyldimethylsilyloxy-1-phenylthioheptyl)-3,4,5-trimethoxybenzene 
• 123731-60-2 Methanesulfonic acid 1-(2-bromo-3,4,5-trimethoxy-phenyl)-4-(tert-butyl-dimethyl-silanyloxy)-heptyl ester 

Relevant articles and documents

Efficient asymmetric synthesis of chiral alcohols using high 2-propanol tolerance alcohol dehydrogenase: Sm ADH2 via an environmentally friendly TBCR system

Alcohol dehydrogenases (ADHs) together with the economical substrate-coupled cofactor regeneration system play a pivotal role in the asymmetric synthesis of chiral alcohols; however, severe challenges concerning the poor tolerance of enzymes to 2-propanol and the adverse effects of the by-product, acetone, limit its applications, causing this strategy to lapse. Herein, a novel ADH gene smadh2 was identified from Stenotrophomonas maltophilia by traditional genome mining technology. The gene was cloned into Escherichia coli cells and then expressed to yield SmADH2. SmADH2 has a broad substrate spectrum and exhibits excellent tolerance and superb activity to 2-propanol even at 10.5 M (80%, v/v) concentration. Moreover, a new thermostatic bubble column reactor (TBCR) system is successfully designed to alleviate the inhibition of the by-product acetone by gas flow and continuously supplement 2-propanol. The organic waste can be simultaneously recovered for the purpose of green synthesis. In the sustainable system, structurally diverse chiral alcohols are synthesised at a high substrate loading (>150 g L-1) without adding external coenzymes. Among these, about 780 g L-1 (6 M) ethyl acetoacetate is completely converted into ethyl (R)-3-hydroxybutyrate in only 2.5 h with 99.9% ee and 7488 g L-1 d-1 space-time yield. Molecular dynamics simulation results shed light on the high catalytic activity toward the substrate. Therefore, the high 2-propanol tolerance SmADH2 with the TBCR system proves to be a potent biocatalytic strategy for the synthesis of chiral alcohols on an industrial scale.

Synthesis method of ethyl 3-hydroxyhexanoate

The invention discloses a synthesis method of ethyl 3-hydroxyhexanoate. The method is characterized by comprising the following steps: reacting bromine with acetic acid to prepare bromoacetic acid; reacting the bromoacetic acid with ethanol in the presence of sulfuric acid to generate ethyl bromoacetate; adding 500kg of dichloromethane and 140kg of n-butyraldehyde into a reaction kettle; adding acatalyst, heating to reflux, dropwise adding 250kg of the ethyl bromoacetate serving as a product obtained in the previous step, controlling the dropwise adding speed, controlling the adding to be completed within 3 hours in a reflux state, preserving heat for 2 hours, cooling to room temperature, washing to neutrality, transferring into a rectifying tower, and rectifying to obtain a qualified product, namely the ethyl 3-hydroxyhexanoate.

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