21188-58-9

Basic information

• Product Name: FEMA 3508
• Synonyms: 3-hydroxy-hexanoicacimethylester;METHYL-3-HYDROXYCAPROATE;METHYL 3-HYDROXYHEXANOATE;HEXANOIC ACID, 3-HYDROXY-, METHYL ESTER;FEMA 3508;3-HYDROXY C6:0 METHYL ESTER;METHYL 3-HYDROXYHEXANOATE 97+%;3-Hydroxyhexanoic acid methyl ester
• CAS NO: 21188-58-9
• Molecular Formula: C₇H₁₄O₃
• Molecular Weight: 146.18
• EINECS: 244-261-0
• Product Categories: Alphabetical Listings;Flavors and Fragrances;M-N
• Mol File: 21188-58-9.mol
• Article Data: 17

Chemical Properties

• Boiling Point: 223 °C at 760 mmHg
• Flash Point: 185 °F
• Appearance: /
• Density: 1 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.02mmHg at 25°C
• Refractive Index: n20/D 1.43(lit.)
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 13.95±0.20(Predicted)
• CAS DataBase Reference: FEMA 3508(CAS DataBase Reference)
• NIST Chemistry Reference: FEMA 3508(21188-58-9)
• EPA Substance Registry System: FEMA 3508(21188-58-9)

Safety Data

• Hazard Codes: Xi
• Statements: 41
• Safety Statements: 26-39
• RIDADR: NA 1993 / PGIII
• WGK Germany: 3
• Hazardous Substances Data: 21188-58-9(Hazardous Substances Data)

Usage

Description

FEMA 3508, also known as 3-Hydroxyhexanoic Acid Methyl Ester, is a hydroxylated fatty acid ester that is a volatile component and aromatic agent. It is found in various fruits and juices, such as pineapple, Valencia orange, passion fruit, strawberry, wood apple, soursop, mountain papaya, and naranjilla. FEMA 3508 has an ethereal, wine-like, fruity, and oily aroma, making it a valuable compound in the flavor and fragrance industry.

Uses

Used in the Food Industry:
FEMA 3508 is used as a flavoring compound for its sweet, fruity, overripe, pineapple, and tropical taste with woody nuances. It is commonly used to enhance the flavor of various food products, providing a pleasant and distinctive taste.
Used in the Flavor and Fragrance Industry:
FEMA 3508 is used as an aromatic agent for its ethereal, wine-like, fruity, and oily aroma. It is utilized in the creation of various fragrances and perfumes, adding a unique and captivating scent to the final product.
Used in the Beverage Industry:
FEMA 3508 is used as a flavor enhancer in the beverage industry, particularly in fruit juices and fruit-based drinks. Its natural occurrence in various fruits makes it an ideal choice for adding a fresh and authentic taste to these products.
Used in the Cosmetic Industry:
FEMA 3508 can be used in the cosmetic industry as a fragrance ingredient, providing a pleasant and long-lasting scent to personal care products such as lotions, creams, and perfumes.

InChI:InChI=1/C7H14O3/c1-3-4-6(8)5-7(9)10-2/h6,8H,3-5H2,1-2H3

Upstream product

• 3249-68-1 ethyl butyroyl acetate 
• 9004-34-6 cellulose 
• 133842-18-9 C₁₃H₂₈O₄Si 
• 2396-77-2 methyl 2-hexenoate 
• 105952-80-5 4-(1,1-Dichloro-propyl)-oxetan-2-one 
• 186581-53-3 diazomethane 
• 10191-24-9 3-hydroxyhexanoic acid 
• 30414-54-1 methyl 3-oxohexanoate 
• 117709-02-1 3-propylepoxyethane-2-carboxylic acid methyl ester 
• 100939-31-9 methyl trans-2,3-epoxy-hexanoate 
• 123-72-8 butyraldehyde 
• 96-32-2 bromoacetic acid methyl ester 
• 101392-68-1 4,4-Dichloro-3-hydroxy-hexanoic acid methyl ester 

Downstream Products

• 102882-04-2 3-phenylhexanoic methyl ester 
• 30414-54-1 methyl 3-oxohexanoate 
• 5413-09-2 rac-methyl 3-methoxyhexanoic acid 

Relevant articles and documents

Chemistry of metapleural gland secretions of three attine ants, Atta sexdens rubropilosa, Atta cephalotes, and Acromyrmex octospinosus (Hymenoptera: Formicidae)

The chemical composition of the secretions of the metapleural glands of workers and soldiers of two Atta species, atta sexdens rubropilosa and A. cephalotes, and workers of Acromyrmex oetospinoxus, has been studied. As indicated by infrared spectrometry and confirmed by the ninhydrin test, the secretions contain chiefly proteins. Of the volatile acidic portion, which is present as ionized salts, phenylacetic acid is the major component in workers and soldiers of A. s. rubropilosa and A. cephalotes. Both Atta species also contain 3 hydroxydecanoic acid and its homolog as minor components together with indoleacetic acid. While there are qualitative similarities in the acidic composition in the secretions of A. s. rubropilosa and A. cephalotes, they differ quantitatively. The secretion of Acromyrmex octospinosus contains 3-hydoxydecanoic and indoleacetic acids, but lacks phenylacetic acid The bactericidal and fungicidal actions of the three major substances have been confirmed.

Diastereoselective Synthesis of 2,5-Dialkyl Tetrahydrofuran-3-ones by a Copper-Catalysed Tandem Carbenoid Insertion and Ylide Rearrangement Reaction

Cu(acac)2-catalysed cyclisations of the α-diazo ketones 3, result in the diastereoselective formation (>97:3) of the trans-2,5-dialkyl tetrahydrofuran-3-ones 4.The yields and levels of diastereoselection are catalyst, solvent, and temperature dependent.

ASYMMETRIC SYNTHESIS OF (S)-METHYL-3-HYDROXYALKANOATES FROM KETENE AND 2,2-DICHLOROALDEHYDES VIA 4-(1,1-DICHLOROALKYL)-2-OXETANONES

Using the quinidine catalyzed cycloaddition reaction of ketene and 2,2-dichloroaldehydes, the preparation of several optically pure (S)-methyl-3-hydroxyalkanoates is reported.

Inversion of cpADH5 Enantiopreference and Altered Chain Length Specificity for Methyl 3-Hydroxyalkanoates

Expanding the substrate scope of enzymes opens up new routes for synthesis of valuable chemicals. Ketone-functionalized fatty acid derivatives and corresponding chiral alcohols are valuable building blocks for the synthesis of a variety of chemicals including pharmaceuticals. The alcohol dehydrogenase from Candida parapsilosis (cpADH5) catalyzes the reversible oxidations of chiral alcohols and has a broad substrate range; a challenge for cpADH5 is to convert alcohols with small substituents (methyl or ethyl) next to the oxidized alcohol moiety. Molecular docking studies revealed that W286 is located in the small binding pocket and limits the access to substrates that contain aliphatic chains longer than ethyl substituent. In the current manuscript, we report that positions L119 and W286 are key residues to boost oxidation of medium chain methyl 3-hydroxy fatty acids; interestingly the enantiopreference toward methyl 3-hydroxybutyrate was inverted. Kinetic characterization of W286A showed a 5.5 fold increase of Vmax and a 9.6 fold decrease of Km values toward methyl 3-hydroxyhexanoate (Vmax: 2.48 U mg? and Km: 4.76 mm). Simultaneous saturation at positions 119 and 286 library yielded a double mutant (L119M/W286S) with more than 30-fold improved activity toward methyl 3-hydroxyoctanoate (WT: no conversion; L119M/W286S: 30 %) and inverted enantiopreference (S-enantiomer ≥99 % activity decrease and R-enantiomer >20-fold activity improvement) toward methyl 3-hydroxybutyrate.

The synthesis of medium-chain-length β-hydroxy esters via the reformatsky reaction

The synthesis of medium-chain-length β-hydroxy esters in good yield via the Reformatsky reaction is described. This work will be used as the basis for further investigation of hydroxyalkanoate polymers as potential feedstock for biofuel production.