Ethyl (R)-(-)-mandelate

Base Information

• Chemical Name: Ethyl (R)-(-)-mandelate
• CAS No.: 10606-72-1
• Molecular Formula: C10H12O3
• Molecular Weight: 180.203
• Hs Code.: 2918199090
• DSSTox Substance ID: DTXSID30147492
• Nikkaji Number: J74.079I
• Wikidata: Q27147809
• Mol file: 10606-72-1.mol

Synonyms:Ethyl (R)-(-)-mandelate;10606-72-1;ethyl (2R)-2-hydroxy-2-phenylacetate;(R)-Ethyl 2-hydroxy-2-phenylacetate;ethyl(r)-(-)-mandelate;D-(-)-Mandelic Acid Ethyl Ester;ethyl (2R)-hydroxy(phenyl)acetate;(c)zR(c){-(-)-Ethyl mandelate;ethyl (R)-(-)-2-hydroxy-2-phenylacetate;Benzeneacetic acid, alpha-hydroxy-, ethyl ester, (R)-;Ethyl hydroxy(phenyl)acetate #;MFCD00064248;ethyl r-mandelate;ethyl-(R)-mandelate;(-)-Ethyl mandelate;D-Mandelic acid ethyl;Ethyl D-(-)-Mandelate;Benzeneacetic acid, .alpha.-hydroxy-, ethyl ester, (R)-;SCHEMBL3266292;CHEBI:78406;DTXSID30147492;_x000D_Ethyl (R)-(-)-Mandelate;AKOS015969280;AS-31055;CS-0143521;M1344;Benzeneacetic acid,a-hydroxy-,ethyl ester,(ar)-;J-001538;Q27147809;Ethyl (R)-(-)-mandelate, 99%, optical purity ee: 99% (GLC)

Chemical Property of Ethyl (R)-(-)-mandelate

Chemical Property:

• Appearance/Colour: liquid
• Vapor Pressure: 0.00918mmHg at 25°C
• Melting Point: 33-34 °C(lit.)
• Refractive Index: -137.5 ° (C=1, CHCl3)
• Boiling Point: 253.999 °C at 760 mmHg
• PKA: 12.33±0.20(Predicted)
• Flash Point: 118.069 °C
• PSA: 46.53000
• Density: 1.148 g/cm³
• LogP: 1.28310
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 180.078644241
• Heavy Atom Count: 13
• Complexity: 162

Purity/Quality:

98%,99%, ^*data from raw suppliers

Ethyl (R)-(?)-mandelate ^*data from reagent suppliers

Safty Information:

• Safety Statements: S24/25:Avoid contact with skin and eyes.

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C(C1=CC=CC=C1)O
• Isomeric SMILES: CCOC(=O)[C@@H](C1=CC=CC=C1)O

Technology Process of Ethyl (R)-(-)-mandelate

There total 48 articles about Ethyl (R)-(-)-mandelate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.0%

ethanol (64-17-5) + (R)-Mandelic Acid (611-71-2) → (R)-mandelic acid ethyl ester (10606-72-1)

Guidance literature:

With boron trifluoride diethyl etherate; for 1h; Heating;

DOI:10.1016/S0040-4020(99)00267-7

Reference yield: 97.0%

phenylglyoxylic acid ethyl ester (1603-79-8) → (R)-mandelic acid ethyl ester (10606-72-1)

Guidance literature:

With magnesium(II); In dichloromethane; at 20 ℃; for 16h;

DOI:10.1016/S0957-4166(00)00248-2

Reference yield: 95.0%

phenylglyoxylic acid ethyl ester (1603-79-8) → (R)-mandelic acid ethyl ester (10606-72-1) + (S)-(-)-ethyl mandelate (13704-09-1)

Guidance literature:

With D-glucose; Bacillus megaterium glucose dehydrogenase; Pichia glucozyma CBS 5766 recombinant NADPH-dependent benzil reductase; NADPH; In dimethyl sulfoxide; at 25 ℃; for 0.5h; pH=8; Enzymatic reaction;

DOI:10.1007/s00253-015-6961-y

upstream raw materials:

ethanol

(R)-Mandelic Acid

phenylglyoxylic acid ethyl ester

(1-ethoxy-2-phenylvinyloxy)trimethylsilane

Downstream raw materials:

1-phenyl-2-propyl-pentane-1,2-diol

(R)-1-carbethoxy-1-phenylmethyl phosphorodichloridite

(R)-α-hydroxyphenylacetylhydrazine

(S)-2-chloro-2-phenylacetic acid ethyl ester

Refernces

• 1、 Burgess, Vicky A.,Davies, Stephen G.,Skerlj, Renato T.,Whittaker, Mark. "Chiral organometallic NADH mimics: Highly stereoselective reductions of ethyl benzoylformate with a 1,4-dihydronicotinoyl fragment attached to the homochiral auxiliary 5-C5H5)Fe(CO)(PPh3)> and possessing a homochiral β-hydroxy-carboxamide at C-5.". . p. 871 - 901. Retrieved 1992.
• 2、 Gran, Ulrik,Wennerstroem, Olof,Westman, Gunnar. "Stereoselective reductions with macrocyclic NADH models". . p. 3027 - 3040. Retrieved 2000.
• 3、 Diezi, Simon,Reimann, Sven,Bonalumi,Mallat, Tamas,Baiker, Alfons. "Steric and electronic effects in the enantioselective hydrogenation of activated ketones on platinum: Directing effect of ester group". . p. 255 - 262. Retrieved 2006.
• 4、 Zhu, Dunming,Stearns, Jennifer Elisabeth,Ramirez, Monica,Hua, Ling. "Enzymatic enantioselective reduction of α-ketoesters by a thermostable 7α-hydroxysteroid dehydrogenase from Bacteroides fragilis". . p. 4535 - 4539. Retrieved 2006.
• 5、 Peng, Yongwu,Gong, Tengfei,Cui, Yong. "A homochiral porous metal-organic framework for enantioselective adsorption of mandelates and photocyclizaton of tropolone ethers". . p. 8253 - 8255. Retrieved 2013.
• 6、 Ross. "-". . p. 718,720. Retrieved 1936.
• 7、 Stockinger, Skrollan,Troendlin, Johannes,Rominger, Frank,Trapp, Oliver. "On-Column Reaction Set-Up for High-Throughput Screenings and Mechanistic Investigations". . p. 3513 - 3520. Retrieved 2015.
• 8、 Brown, Herbert C.,Cho, Byung Tae,Park, Won Suh. "Asymmetric Reduction of α-Keto Esters with Potassium 9-O-(1,2:5,6-Di-O-isopropylidene-α-D-glucofuranosyl)-9-boratabicyclononane. Chiral Synthesis of α-Hydroxy Esters with Optical Purity Approaching 100percent ee". . p. 3396 - 3398. Retrieved 1986.
• 9、 Shumilov, Vladimir,Kirilin, Alexey,Tokarev, Anton,Boden, Stephan,Schubert, Markus,Hampel, Uwe,Hupa, Leena,Salmi, Tapio,Murzin, Dmitry Yu.. "Preparation of γ-Al2O3/α-Al2O3 ceramic foams as catalyst carriers via the replica technique". . p. 64 - 73. Retrieved 2022.
• 10、 Ishihara, Kohji,Nakajima, Nobuyoshi. "Stereoselective reduction of carbonyl compounds using the cell-free extract of the earthworm, Lumbricus rubellus, as a novel source of biocatalyst". . p. 3077 - 3080. Retrieved 2006.