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METHYL (2S)-GLYCIDATE, also known as methyl (S)-2,3-epoxypropionate, is a colorless liquid chemical compound with the molecular formula C4H6O3. It is characterized by a fruity odor and is commonly used in various applications due to its unique properties.

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  • methyl (2S)-oxirane-2-carboxylate;Methyl (2S)-glycidate;2-Oxiranecarboxylicacid,methyl ester,(2S);Methyl (S)-oxiranecarboxylate;(s)-methyloxirane-2-carboxylate;methyl (R)-oxiranecarboxylate;

    Cas No: 118712-39-3

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  • methyl (2S)-oxirane-2-carboxylate;Methyl (2S)-glycidate;2-Oxiranecarboxylicacid,methyl ester,(2S);Methyl (S)-oxiranecarboxylate;(s)-methyloxirane-2-carboxylate;methyl (R)-oxiranecarboxylate;

    Cas No: 118712-39-3

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  • methyl (2S)-oxirane-2-carboxylate;Methyl (2S)-glycidate;2-Oxiranecarboxylicacid,methyl ester,(2S);Methyl (S)-oxiranecarboxylate;(s)-methyloxirane-2-carboxylate;methyl (R)-oxiranecarboxylate;

    Cas No: 118712-39-3

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  • methyl (2S)-oxirane-2-carboxylate;Methyl (2S)-glycidate;2-Oxiranecarboxylicacid,methyl ester,(2S);Methyl (S)-oxiranecarboxylate;(s)-methyloxirane-2-carboxylate;methyl (R)-oxiranecarboxylate;

    Cas No: 118712-39-3

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  • 118712-39-3 Structure
  • Basic information

    1. Product Name: METHYL (2S)-GLYCIDATE
    2. Synonyms: (S)-METHYLGLYCIDATE;(2S)-METHYLGLYCIDATE;METHYL-(S)-OXIRANECARBOXYLATE;METHYL (2S)-GLYCIDATE;Methyl (2S)-2,3-epoxypropanoate;Methyl-2,3-epoxypropanoate;Methyl (2S)-oxirane-2-carboxylate;Methyl (2S)-glycidate optical purity ee: 99% (GLC), 98%
    3. CAS NO:118712-39-3
    4. Molecular Formula: C4H6O3
    5. Molecular Weight: 102.09
    6. EINECS: N/A
    7. Product Categories: N/A
    8. Mol File: 118712-39-3.mol
  • Chemical Properties

    1. Melting Point: N/A
    2. Boiling Point: 97.45 °C at 760 mmHg
    3. Flash Point: 72 °C
    4. Appearance: /
    5. Density: 1.166 g/mL at 25 °C(lit.)
    6. Vapor Pressure: 41.693mmHg at 25°C
    7. Refractive Index: n20/D 1.42(lit.)
    8. Storage Temp.: 2-8°C
    9. Solubility: N/A
    10. CAS DataBase Reference: METHYL (2S)-GLYCIDATE(CAS DataBase Reference)
    11. NIST Chemistry Reference: METHYL (2S)-GLYCIDATE(118712-39-3)
    12. EPA Substance Registry System: METHYL (2S)-GLYCIDATE(118712-39-3)
  • Safety Data

    1. Hazard Codes: Xi
    2. Statements: 36/37/38
    3. Safety Statements: 26-36
    4. RIDADR: NA 1993 / PGIII
    5. WGK Germany: 3
    6. RTECS:
    7. HazardClass: N/A
    8. PackingGroup: N/A
    9. Hazardous Substances Data: 118712-39-3(Hazardous Substances Data)

118712-39-3 Usage

Uses

Used in Flavor and Fragrance Industry:
METHYL (2S)-GLYCIDATE is used as a flavoring agent and fragrance in products such as perfumes, soaps, and cosmetics for its fruity odor, enhancing the sensory experience of these products.
Used in Pharmaceutical Industry:
METHYL (2S)-GLYCIDATE is used as an intermediate in the production of pharmaceuticals, contributing to the synthesis of various medicinal compounds.
Used in Agrochemical Industry:
METHYL (2S)-GLYCIDATE is used in the production of agrochemicals, playing a role in the development of agricultural products to improve crop yield and protection.
Used as a Solvent in Chemical Synthesis:
METHYL (2S)-GLYCIDATE serves as a solvent in chemical synthesis processes, facilitating reactions that require a suitable medium to proceed efficiently.
It is important to handle METHYL (2S)-GLYCIDATE with care due to its potential to cause irritation to the skin, eyes, and respiratory system, and its harmful effects if ingested or inhaled.

Check Digit Verification of cas no

The CAS Registry Mumber 118712-39-3 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,1,8,7,1 and 2 respectively; the second part has 2 digits, 3 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 118712-39:
(8*1)+(7*1)+(6*8)+(5*7)+(4*1)+(3*2)+(2*3)+(1*9)=123
123 % 10 = 3
So 118712-39-3 is a valid CAS Registry Number.
InChI:InChI=1/C4H6O3/c1-6-4(5)3-2-7-3/h3H,2H2,1H3/t3-/m0/s1

118712-39-3 Well-known Company Product Price

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  • Aldrich

  • (469432)  Methyl(2S)-glycidate  optical purity ee: 99% (GLC), 98%

  • 118712-39-3

  • 469432-5G

  • 3,129.75CNY

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  • Aldrich

  • (469432)  Methyl(2S)-glycidate  optical purity ee: 99% (GLC), 98%

  • 118712-39-3

  • 469432-25G

  • 9,114.30CNY

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118712-39-3SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 18, 2017

Revision Date: Aug 18, 2017

1.Identification

1.1 GHS Product identifier

Product name methyl (2S)-oxirane-2-carboxylate

1.2 Other means of identification

Product number -
Other names Methyl (2S)-glycidate

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:118712-39-3 SDS

118712-39-3Relevant articles and documents

Synthesis of the fungal macrolide berkeleylactone A and its inhibition of microbial biofilm formation

Schobert, Rainer,Schrey, Hedda,Schriefer, Manuel G.,Stadler, Marc,Zeng, Haoxuan

, p. 4743 - 4751 (2021/06/11)

The fungal macrolide berkeleylactone A was synthesised in 13 steps and 24% yield using (R)-propylene oxide and an asymmetric Noyori hydrogenation of a β-ketoester to install the stereogenic centres. A domino addition-Wittig olefination of a 13-hydroxytetradecanal intermediate with the cumulated ylide Ph3PCCO closed the macrocyle by establishing the α,β-unsaturated ester group, necessary for the attachment of the sidechain thiol via a thia-Michael reaction. The synthetic berkeleylactone A inhibited the formation of Staphylococcus aureus biofilms and showed significant dispersive effects on preformed biofilms of Candida albicans by at least 45% relative to untreated controls at concentrations as low as 1.3 μg mL-1.

Aromatic Donor-Acceptor Interaction-Based Co(III)-salen Self-Assemblies and Their Applications in Asymmetric Ring Opening of Epoxides

Liang, Jian,Soucie, Luke N.,Blechschmidt, Daniel R.,Yoder, Aaron,Gustafson, Addie,Liu, Yu

supporting information, p. 513 - 518 (2019/01/14)

Aromatic donor-acceptor interaction as the driving force to assemble cooperative catalysts is described. Pyrene/naphthalenediimide functionalized Co(III)-salen complexes self-assembled into bimetallic catalysts through aromatic donor-acceptor interactions and showed high catalytic activity and selectivity in the asymmetric ring opening of various epoxides. Control experiments, nuclear magnetic resonance (NMR) spectroscopy titrations, mass spectrometry measurement, and X-ray crystal structure analysis confirmed that the catalysts assembled based on the aromatic donor-acceptor interaction, which can be a valuable noncovalent interaction in supramolecular catalyst development.

The asymmetric total synthesis of (+)-salvianolic acid A

Zheng, Yong,Song, Wei-Bin,Xuan, Li-Jiang

supporting information, p. 5047 - 5050 (2016/07/25)

An asymmetric synthesis of (+)-salvianolic acid A with cardioprotective properties, has been accomplished in a convergent manner in eight steps and 10.6% overall yield. This synthesis features an asymmetric addition of organometallics to optically pure 2,3-epoxypropionate in the presence of BF3·Et2O, Ru(III)-catalyzed directed [Formula presented] olefination, and I2-catalyzed isomerization reaction.

A broadly applicable and practical oligomeric (salen)Co catalyst for enantioselective epoxide ring-opening reactions

White, David E.,Tadross, Pamela M.,Lu, Zhe,Jacobsen, Eric N.

supporting information, p. 4165 - 4180 (2014/06/09)

The (salen)Co catalyst (4a) can be prepared as a mixture of cyclic oligomers in a short, chromatography-free synthesis from inexpensive, commercially available precursors. This catalyst displays remarkable enhancements in reactivity and enantioselectivity relative to monomeric and other multimeric (salen)Co catalysts in a wide variety of enantioselective epoxide ring-opening reactions. The application of catalyst 4a is illustrated in the kinetic resolution of terminal epoxides by nucleophilic ring-opening with water, phenols, and primary alcohols; the desymmetrization of meso epoxides by addition of water and carbamates; and the desymmetrization of oxetanes by intramolecular ring opening with alcohols and phenols. The favorable solubility properties of complex 4a under the catalytic conditions facilitated mechanistic studies, allowing elucidation of the basis for the beneficial effect of oligomerization. Finally, a catalyst selection guide is provided to delineate the specific advantages of oligomeric catalyst 4a relative to (salen)Co monomer 1 for each reaction class.

NEW CHIRAL SALEN CATALYSTS AND METHODS FOR THE PREPARATION OF CHIRAL COMPOUNDS FROM RACEMIC EPOXIDES BY USING THEM

-

Page/Page column 39; 40, (2009/01/24)

The present invention relates to new chiral salen catalysts and the preparation method of chiral compounds from racemic epoxides using the same. More specifically, it relates to new chiral salen catalysts that have high catalytic activity due to new molecular structures and have no or little racemization of the generated target chiral compounds even after the reaction is completed and can be also reused without catalyst regeneration treatment, and its economical preparation method to mass manufacture chiral compounds of high optical purity, which can be used as raw materials for chiral food additives, chiral drugs, or chiral crop protection agents, etc., using the new chiral salen catalysts.

Hydrolytic kinetic resolution of epoxides catalyzed by chromium(III)-endo, endo-2,5-diaminonorbornane-salen [Cr(III)-DIANANE-salen] complexes. Improved activity, low catalyst loading

Berkessel, Albrecht,Ertuerk, Erkan

, p. 2619 - 2625 (2007/10/03)

The hydrolytic kinetic resolution (HKR) of terminal epoxides, using chiral chromium(III)-salen catalysts based on DIANANE (endo,endo-2,5-diaminonorbornane) , was studied. A broad substrate scope was found for the chromium(III)-DIANANE catalysts, and very low loadings (down to 0.05 mol%) were needed to achieve high enantiomeric purities of both the remaining epoxides and the product diols (up to >99% ee). Besides monosubstituted epoxides, 2-methyl-2-n-pentyloxirane, which is an example for 2,2-disubstituted epoxides, could be ring-opened in an asymmetric fashion with water in the presence of an electronically tuned chromium-(III)-DIANANE complex.

Inhibition of the severe acute respiratory syndrome 3CL protease by peptidomimetic α,β-unsaturated esters

Shie, Jiun-Jie,Fang, Jim-Min,Kuo, Tun-Hsun,Kuo, Chih-Jung,Liang, Po-Huang,Huang, Hung-Jyun,Wu, Yin-Ta,Jan, Jia-Tsrong,Cheng, Yih-Shyun E.,Wong, Chi-Huey

, p. 5240 - 5252 (2007/10/03)

The proteolytic processing of polyproteins by the 3CL protease of severe acute respiratory syndrome coronavirus is essential for the viral propagation. A series of tripeptide α,β-unsaturated esters and ketomethylene isosteres, including AG7088, are synthesized and assayed to target the 3CL protease. Though AG7088 is inactive (IC50 > 100 μM), the ketomethylene isosteres and tripeptide α,β-unsaturated esters containing both P1 and P2 phenylalanine residues show modest inhibitory activity (IC50 = 11-39 μM). The Phe-Phe dipeptide inhibitors 18a-e are designed on the basis of computer modeling of the enzyme-inhibitor complex. The most potent inhibitor 18c with an inhibition constant of 0.52 μM is obtained by condensation of the Phe-Phe dipeptide α,β-unsaturated ester with 4-(dimethylamino)cinnamic acid. The cell-based assays also indicate that 18c is a nontoxic anti-SARS agent with an EC50 value of 0.18 μM.

Mechanistic Investigation Leads to a Synthetic Improvement in the Hydrolytic Kinetic Resolution of Terminal Epoxides

Nielsen, Lars P. C.,Stevenson, Christian P.,Blackmond, Donna G.,Jacobsen, Eric N.

, p. 1360 - 1362 (2007/10/03)

The mechanism of the hydrolytic kinetic resolution (HKR) of terminal epoxides was investigated by kinetic analysis using reaction calorimetry. The chiral (salen)Co-X complex (X = OAc, OTs, Cl) undergoes irreversible conversion to (salen)Co-OH during the course of the HKR and thus serves as both precatalyst and cocatalyst in a cooperative bimetallic catalytic mechanism. This insight led to the identification of more active catalysts for the HKR of synthetically useful terminal epoxides. Copyright

New oligomeric catalyst for the hydrolytic kinetic resolution of terminal epoxides under solvent-free conditions

White, David E.,Jacobsen, Eric N.

, p. 3633 - 3638 (2007/10/03)

The solvent-free hydrolytic kinetic resolution of terminal epoxides catalyzed by a new oligomeric (salen)Co complex 2 is described. Extremely low loadings of catalyst were used to provide all epoxides examined in good yields and >99% ee under ambient conditions within 24 h.

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