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
• Article Data: 64

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

Chemical Properties

Different sources of media describe the Chemical Properties of 2305-25-1 differently. You can refer to the following data:
1. Colorless clear liquid
2. Ethyl 3-hydroxyhexanoate has a fruity odor.

Occurrence

Reported found in citrus, grape, orange, grapefruit and tangerine juice, orange peel oil, pineapple, strawberry, cognac, Scotch whiskey, red and white wine, passion fruit, mango, quince, wood apple, mountain papaya, pawpaw and hog plum (Spondias mombins L.).

Uses

Ethyl 3-Hydroxyhexanoate is a general volatile organic compound which contributes to the scent and flavor profile of various fruits such as guava fruit and bananas.

Definition

ChEBI: A fatty acid ester that is the ethyl ester of 3-hydroxyhexanoic acid.

Taste threshold values

Taste characteristics at 80 ppm: sweet, fruity, grape with citrus notes.

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

• 123-72-8 butyraldehyde 
• 105-36-2 ethyl bromoacetate 
• 927-80-0 1-ethoxyacetylene 
• 3249-68-1 ethyl butyroyl acetate 
• 623-48-3 ethyl iodoacetae 
• 141-78-6 ethyl acetate 
• 61454-93-1 ethyl 3-propyloxirane-2-carboxylate 
• 64-17-5 ethanol 
• 66997-60-2 (+)-(3S)-3-hydroxyhexanoic acid 
• 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 

Downstream Products

• 345922-13-6 5-hydroxy-3-oxo-2-(triphenyl-λ⁵-phosphanylidene)-octanenitrile 
• 345922-12-5 acetic acid 4-cyano-3-oxo-1-propyl-4-(triphenyl-λ⁵-phosphanylidene)-butyl ester 
• 345922-11-4 5-(tert-butyl-dimethyl-silanyloxy)-3-oxo-2-(triphenyl-λ⁵-phosphanylidene)-octanenitrile 
• 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 

Relevant articles and documents

Organic Sonochemistry. Sonic Acceleration of the Reformatsky Reaction

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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.

Synthesis of Thelepamide via Catalyst-Controlled 1,4-Addition of Cysteine Derivatives and Structure Revision of Thelepamide

The first enantioselective total synthesis and structural reassignment of (-)-thelepamide, a cytotoxic tetraketide-amino acid from the marine worm Thelepus crispus, is reported. A convergent approach provides access to all thelepamide diastereomers in six steps from four simple building blocks. Key features of the synthesis include the application of Melchiorre's organocatalytic thia-Michael reaction and a sonication-assisted assembly of an unprecedented N,O-acetal-hemiacetal moiety. The corrected structure was confirmed by NMR-DFT analysis.