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(R)-Ethyl-2-hydroxypentanoate, with the molecular formula C7H14O3, is a colorless liquid characterized by a sweet, fruity odor. It is a chiral compound, featuring two enantiomers, (R)and (S)forms, with the (R)-form predominantly utilized in commercial applications. Derived from natural sources, it is deemed safe for use in the food and cosmetic industries, showcasing its versatility as a chemical compound with a spectrum of industrial and commercial applications.

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  • 115626-59-0 Structure
  • Basic information

    1. Product Name: (R)-Ethyl-2-hydroxypentanoate
    2. Synonyms: (R)-Ethyl-2-hydroxypentanoate;ethyl(R)-2-hydroxypentanoate;EOS-61183
    3. CAS NO:115626-59-0
    4. Molecular Formula: C7H14O3
    5. Molecular Weight: 146.185
    6. EINECS: N/A
    7. Product Categories: N/A
    8. Mol File: 115626-59-0.mol
  • Chemical Properties

    1. Melting Point: N/A
    2. Boiling Point: N/A
    3. Flash Point: N/A
    4. Appearance: /
    5. Density: N/A
    6. Refractive Index: N/A
    7. Storage Temp.: N/A
    8. Solubility: N/A
    9. CAS DataBase Reference: (R)-Ethyl-2-hydroxypentanoate(CAS DataBase Reference)
    10. NIST Chemistry Reference: (R)-Ethyl-2-hydroxypentanoate(115626-59-0)
    11. EPA Substance Registry System: (R)-Ethyl-2-hydroxypentanoate(115626-59-0)
  • Safety Data

    1. Hazard Codes: N/A
    2. Statements: N/A
    3. Safety Statements: N/A
    4. WGK Germany:
    5. RTECS:
    6. HazardClass: N/A
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 115626-59-0(Hazardous Substances Data)

115626-59-0 Usage

Uses

Used in the Food Industry:
(R)-Ethyl-2-hydroxypentanoate is used as a flavoring agent for its sweet, fruity odor, enhancing the taste and aroma of various food products.
Used in the Perfume Industry:
It serves as a key component in the production of perfumes, capitalizing on its sweet, fruity scent to contribute to the overall fragrance profile of the product.
Used as a Solvent in Chemical Processes:
(R)-Ethyl-2-hydroxypentanoate is employed as a solvent in various chemical processes, leveraging its properties to facilitate reactions and improve efficiency in the production of different chemicals and compounds.
Used in the Cosmetic Industry:
It is utilized in the formulation of cosmetic products, taking advantage of its natural derivation and safety profile to ensure the well-being of consumers while also enhancing the product's sensory attributes.

Check Digit Verification of cas no

The CAS Registry Mumber 115626-59-0 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,1,5,6,2 and 6 respectively; the second part has 2 digits, 5 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 115626-59:
(8*1)+(7*1)+(6*5)+(5*6)+(4*2)+(3*6)+(2*5)+(1*9)=120
120 % 10 = 0
So 115626-59-0 is a valid CAS Registry Number.

115626-59-0SDS

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 ethyl (2R)-2-hydroxypentanoate

1.2 Other means of identification

Product number -
Other names ethyl (3R)-hydroxyvalerate

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
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:115626-59-0 SDS

115626-59-0Relevant articles and documents

Asymmetric Synthesis of N-Substituted α-Amino Esters from α-Ketoesters via Imine Reductase-Catalyzed Reductive Amination

Yao, Peiyuan,Marshall, James R.,Xu, Zefei,Lim, Jesmine,Charnock, Simon J.,Zhu, Dunming,Turner, Nicholas J.

supporting information, p. 8717 - 8721 (2021/03/16)

N-Substituted α-amino esters are widely used as chiral intermediates in a range of pharmaceuticals. Here we report the enantioselective biocatalyic synthesis of N-substituted α-amino esters through the direct reductive coupling of α-ketoesters and amines employing sequence diverse metagenomic imine reductases (IREDs). Both enantiomers of N-substituted α-amino esters were obtained with high conversion and excellent enantioselectivity under mild reaction conditions. In addition >20 different preparative scale transformations were performed highlighting the scalability of this system.

SARTAN ANALOGUE

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Page/Page column 9; 10; 18; 21; 22, (2019/07/23)

The invention concerns a sartan analogue on basis of a sartan which sartan comprises an alkyl group or an alkoxy group, wherein the sartan analogue only differs from the sartan by a replacement of the alkyl group or the alkoxy group or replacement of a methyl residue or a hydrogen residue of the alkyl group or of the alkoxy group by a fluorine atom.

A method for synthesis of 1, 2 - pentanediol (by machine translation)

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Paragraph 0025; 0030; 0035; 0040; 0042; 0045; 0050, (2018/10/19)

The invention relates to the field of organic synthetic technology, in particular to a 1, 2 - pentanediol synthetic method, comprises the following steps: (1) heating the raw material-butyraldehyde, adjusting the pH after adding the hydrocyanic acid, obtained by the reaction of 2 - hydroxy pentanonitrile; (2) taking step (1) in 2 - hydroxy pentanonitrile, adding an alcohol as a solvent to stir and mix, add water to stir and mix, hydrogen chloride gas, in 5 °C the following reaction under the condition for a period of time, to continue the reaction temperature, after the reaction product after the neutralization reaction, centrifugal separation, obtained after the distillation is 2 - hydroxy valeric acid ester compound; (3) heating the step (2) in 2 - hydroxy valeric acid ester compound, under the effects of catalyst after hydrogenation reaction to obtain the 1, 2 - pentanediol. Using the synthesis method of the invention, the 1, 2 - pentanediol yield, and reduces the production cost. (by machine translation)

Enantioselective catalytic synthesis of ethyl mandelate derivatives using Rh(I)-NHC catalysts and organoboron reagents

Marques, Carolina S.,Burke, Anthony J.

, p. 628 - 632 (2013/07/19)

Herein we describe for the first time the enantioselective catalytic arylation of ethyl glyoxalate using phenylboron reagents and chiral rhodium(I)-NHC catalysts. KOtBu was the base of choice, along with tert-amyl alcohol as the solvent. A novel chiral bis-imidazolium salt was synthesized and evaluated for the first time in this catalytic transformation. Although moderate enantioselectivities (up to 34% ee) were obtained for the phenylation reaction, despite the excellent yields, very low enantioselectivities were obtained using other arylboronic acids with a variety of chiral rhodium(I)-NHC catalysts.

Expeditious and novel synthesis of α-hydroxyesters via rhodium-NHC catalyzed arylation of ethyl glyoxalate

Marques, Carolina S.,Burke, Anthony J.

experimental part, p. 7211 - 7216 (2012/09/05)

The rhodium-NHC catalyzed arylation reaction of ethyl glyoxalate with aryl and alkyl boronic acids provides an efficient method for the synthesis of α-hydroxyesters. A wide range of α-hydroxyesters (up to 12) were prepared in good to excellent yields. KOtBu was the base of choice, along with tert-amyl alcohol as the solvent. As far as we are aware, this is the first report of this catalytic arylation, using rhodium-NHC catalysts with this specific substrate type.

METHOD FOR PRODUCING OPTICALLY ACTIVE 2-HYDROXY ESTER AND NOVEL INTERMEDIATE COMPOUND

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Page/Page column 11, (2012/01/13)

Disclosed is a method for producing an optically active 2-hydroxy ester, comprising selectively esterifying one enantiomer of a racemic 2-hydroxy ester in a solvent containing a catalyst such as tetramisole or benzotetramisole, and a carboxylic acid anhydride, or a carboxylic acid anhydride and a carboxylic acid. In particular, in the case where the solvent contains a carboxylic acid anhydride, but does not contain a carboxylic acid, as the carboxylic acid anhydride, a carboxylic acid anhydride containing a tertiary or quaternary carbon atom in the a-position is used. On the other hand, in the case where the solvent contains a carboxylic acid anhydride and a carboxylic acid, as the carboxylic acid, a carboxylic acid containing a tertiary or quaternary carbon atom in the a-position is used.

Kinetic resolution of the racemic 2-hydroxyalkanoates using the enantioselective mixed-anhydride method with pivalic anhydride and a chiral acyl-transfer catalyst

Shiina, Isamu,Nakata, Kenya,Ono, Keisuke,Sugimoto, Masuhiro,Sekiguchi, Akihiro

supporting information; experimental part, p. 167 - 172 (2010/03/26)

A variety of optically active 2-hydroxyalkanoates and the corresponding 2-acyloxyalkanoates are produced by the kinetic resolution of racemic 2-hydroxyalkanoates by using achiral 2,2-diarylacetic acid with hindered carboxylic anhydrides as the coupling reagents. The combined use of diphenylacetic acid, pivalic anhydride, and (+)-(R)-benzotetramisole ((R)-BTM) effectively produces (S)-2-hydroxyalkanoates and (R)-2-acyloxyalkanoates from the racemic 2-hydroxyalkanoates (s-values = 47-202). This protocol directly provides the desired chiral 2-hydroxyalkanoate derivatives from achiral diarylacetic acid and racemic secondary alcohols that do not include the sec-phenethyl alcohol moiety by using the transacylation process to generate the mixed anhydrides from the acid components with bulky carboxylic anhydrides under the influence of the chiral acyl-transfer catalyst. The transition state that provides the desired (R)-2-acyloxyalkanoate from (R)-2-hydroxyalkanoate included in the racemic mixture is disclosed by DFT calculations, and the structural features of the transition form are also discussed.

Stereoselective reduction of carbonyl compounds with actinomycete: Purification and characterization of three α-keto ester reductases from Streptomyces avermitilis

Ishihara, Kohji,Kato, Chiaki,Yamaguchi, Hitomi,Iwai, Rieko,Yoshida, Momoko,Ikeda, Natsumi,Hamada, Hiroki,Masuoka, Noriyoshi,Nakajima, Nobuyoshi

body text, p. 3249 - 3257 (2009/04/10)

We achieved the purification of three α-keto ester reductases (Streptomyces avermitilis keto ester reductase, SAKERs-I, -II, and -III) from Streptomyces avermitilis NBRC14893 whole cells. The molecular masses of the native SAKERs-I, -II, and -III were estimated to be 72, 38, and 36 kDa, respectively, by gel filtration chromatography. The subunit molecular masses of SAKERs-I, -II, and -III were also estimated to be 32, 32, and 34 kDa, respectively, by SDS-polyacrylamide gel electrophoresis. The purified SAKERs-II and -III showed a reducing activity for α-keto esters (in particular, for ethyl pyruvate). SAKER-I showed a high reducing activity not only toward the α- and β-keto esters, but also toward α-keto acid. The N-terminal region amino acid sequences of SAKERs-I, -II, and -III were identical to that of a putative oxidoreductase, SAV2750, a putative oxidoreductase, SAV1849, and a putative oxidoreductase, SAV4117, respectively, hypothetical proteins coded on the S. avermitilis genome.

PROCESS FOR PRODUCTION OF 2-HYDROXY ESTERS

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Page/Page column 14, (2010/11/30)

The invention provides an easy and simple process for the production of 2-hydroxy esters from cyanohydrins, specifically, a process for the production of 2-hydroxy esters represented by the general formula (1) (exclusive of ethyl 2-hydroxy-4-phenylbutyrate), characterized by introducing an acid into a mixture comprising a cyanohydrin represented by the general formula (2), an alcohol, an organic solvent and water: [Chemical formula 1] R1 -CH(OH)-COOR2 (1) R1 -CH(OH)(CN) (2) wherein R1 is hydrogen, a substituted or unsubstituted aliphatic hydrocarbon group which has 1 to 12 carbon atoms and may contain oxygen, sulfur, or nitrogen, a substituted or unsubstituted alicyclic hydrocarbon group which has 3 to 12 carbon atoms and may contain oxygen, sulfur, or nitrogen, or a substituted or unsubstituted aryl or aralkyl group which has 3 to 14 carbon atoms and may contain oxygen, sulfur, or nitrogen; and R2 is alkyl which has 1 to 12 carbon atoms and may contain oxygen, sulfur, or nitrogen.

The bakers' yeast reductions of α- and β-keto ester derivatives in the presence of a sulfur compound

Hayakawa, Ryuuichirou,Nozawa, Kazumi,Kimura, Kimihiko,Shimizu, Makoto

, p. 7519 - 7528 (2007/10/03)

Improvement of the enantioselectivity and enhancement of the reactivity were achieved in the bakers' yeast reduction of the α- and β-keto ester derivatives by the addition of a sulfur compound. High enantioselectivity in the bakers' yeast reduction of keto esters was accomplished by using combination of an addition of a sulfur compound with an appropriate selection of the alcohol part of the ester.

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