L-Erythrulose

Base Information

• Chemical Name: L-Erythrulose
• CAS No.: 533-50-6
• Molecular Formula: C4H8O4
• Molecular Weight: 120.105
• Hs Code.: 29400090
• UNII: WKK1W5B83O
• DSSTox Substance ID: DTXSID801019042
• Nikkaji Number: J15.073H
• Wikidata: Q27103403
• Metabolomics Workbench ID: 38854
• Mol file: 533-50-6.mol

Synonyms:erythrulose;erythrulose, (R)-isomer;L-glycero-tetrulose

Chemical Property of L-Erythrulose

Chemical Property:

• Vapor Pressure: 2.8E-06mmHg at 25°C
• Refractive Index: 1.507
• Boiling Point: 349.6 °C at 760 mmHg
• PKA: 12.00±0.20(Predicted)
• Flash Point: 179.4 °C
• PSA: 77.76000
• Density: 1.42g/cm³
• LogP: -2.09900
• Storage Temp.: room temp
• Solubility.: Methanol (Slightly), Water (Slightly)
• XLogP3: -2
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 120.04225873
• Heavy Atom Count: 8
• Complexity: 80.1

Purity/Quality:

76%min ^*data from raw suppliers

L-Erythrulose ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C(C(C(=O)CO)O)O
• Isomeric SMILES: C([C@@H](C(=O)CO)O)O
• Uses: L-Erythrulose is the L-isomer of D-Erythrulose (E650145), a tetrose carbohydrate that is used in various self-tanning cosmetics combined with dihydroxyacetone. L-(+)-Erythrulose is used as a tanning agent in the cosmetics industry and a source of chiral ethyl ketones used in aldo reaction organic synthesis.

Technology Process of L-Erythrulose

There total 41 articles about L-Erythrulose 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: 86.0%

threitol (2319-57-5,10030-58-7,188346-77-2,149-32-6) → L-erythrulose (533-50-6)

Guidance literature:

With [(neocuproine)Pd(OAc)]₂(OTf)₂; oxygen; In water; acetonitrile; at 25 ℃; for 20h; chemoselective reaction;

DOI:10.1021/ja4008694

Reference yield: 68.0%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + dihydroxyacetone (96-26-4,26776-70-5) → L-erythrulose (533-50-6)

Guidance literature:

With D-fructose-6-phosphate aldolase of Escherichia coli Ala₁₂₉Ser mutant; In water; at 25 ℃; for 21h; pH=7.5;

DOI:10.1002/adsc.200900772

Reference yield: 67.0%

D-Serine (312-84-5,83245-15-2) + Glycolaldehyde (141-46-8) → L-erythrulose (533-50-6)

Guidance literature:

With magnesium(II) chloride hexahydrate; flavin adenine dinucleotide (FAD)-containing flavoenzyme from the yeast Rhodotorula gracilis; thiamine pyrophosphate; oxygen; In water; at 25 ℃; for 8h; pH=7; Enzymatic reaction;

DOI:10.1002/adsc.201900109

upstream raw materials:

diazomethane

(R)-2,3-o-isopropylidene-D-glyceroyl chloride

D-erythrose

D-threose

Downstream raw materials:

D-threose

D-erythrose

Glycolaldehyde

carbon dioxide

Refernces

• 1、 Moonmangmee, Duangtip,Adachi, Osao,Shinagawa, Emiko,Toyama, Hirohide,Theeragool, Gunjana,Lotong, Napha,Matsushita, Kazunobu. "L-erythrulose production by oxidative fermentation is catalyzed by PQQ-containing membrane-bound dehydrogenase.". . p. 307 - 318. Retrieved 2002.
• 2、 -. "PROCESSES FOR PREPARING C-4 SUGARS AND KETOSE SUGARS". Page/Page column 37-39. . Retrieved 2021/11/20.
• 3、 L'enfant, Mélanie,Bruna, Felipe,Lorillière, Marion,Ocal, Nazim,Fessner, Wolf-Dieter,Pollegioni, Loredano,Charmantray, Franck,Hecquet, Laurence. "One-Pot Cascade Synthesis of (3S)-Hydroxyketones Catalyzed by Transketolase via Hydroxypyruvate Generated in Situ from d-Serine by d-Amino Acid Oxidase". . p. 2550 - 2558. Retrieved 2019/04/17.