L-sorbosone

Base Information

• Chemical Name: L-sorbosone
• CAS No.: 49865-02-3
• Molecular Formula: C6H10O6
• Molecular Weight: 178.142
• UNII: AA9VR049A2
• Nikkaji Number: J394.213I
• Wikidata: Q27121307
• Metabolomics Workbench ID: 57081
• Mol file: 49865-02-3.mol

Synonyms:L-sorbosone;1-dehydro-L-sorbose;Sorbosone, L-;L-Xylo-hexosulose;2-dehydro-L-gulose;L-xylo-hexos-2-ulose;49865-02-3;AA9VR049A2;UNII-AA9VR049A2;(3S,4R,5S)-3,4,5,6-tetrahydroxy-2-oxohexanal;CHEBI:48657;DCNMIDLYWOTSGK-KVQBGUIXSA-N;C19679;Q27121307

Chemical Property of L-sorbosone

Chemical Property:

• PSA: 115.06000
• LogP: -3.17060
• XLogP3: -2.9
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 5
• Exact Mass: 178.04773803
• Heavy Atom Count: 12
• Complexity: 167

Purity/Quality:

99%, ^*data from raw suppliers

L-Sorbosone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C(C(C(C(C(=O)C=O)O)O)O)O
• Isomeric SMILES: C([C@@H]([C@H]([C@@H](C(=O)C=O)O)O)O)O
• Uses: L-Sorbosone is a compound that can be converted into L-Ascorbic Acid (A786990) by a novel enzyme, L-sorbosone dehydrogenase 1 (SNDH1), which is isolated from Ketogulonicigenium vulgare DSM 4025.

Technology Process of L-sorbosone

There total 38 articles about L-sorbosone 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: 69.0%

glucosazone (534-97-4) → D-glucosone (643-71-0,25990-59-4,26187-86-0,26345-59-5,49865-02-3,54142-77-7,81844-97-5,81844-98-6,81845-00-3,89576-70-5,90457-64-0,1854-25-7)

Guidance literature:

With benzaldehyde; In ethanol; water; acetic acid; for 4.25h; Heating;

DOI:10.1021/jo00207a048

Reference yield:

D-glucose (50-99-7) → furfural (98-01-1) + 5-hydroxymethyl-2-furfuraldehyde (67-47-0) + D-Fructose (57-48-7,18875-34-8) + 2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one (28564-83-2) + D-glucosone (643-71-0,25990-59-4,26187-86-0,26345-59-5,49865-02-3,54142-77-7,81844-97-5,81844-98-6,81845-00-3,89576-70-5,90457-64-0,1854-25-7) + 3-deoxygalactosone (4084-27-9,30382-30-0,50455-94-2,82399-12-0,4134-97-8) + 3-deoxyglucosone (4134-97-8,30382-30-0,50455-94-2,82399-12-0,4084-27-9) + 1-deoxy-2,3-D-erythro-hexo-2,3-diulose + 3-deoxypentos-2-ulose + 1,4-dideoxyhexosulose

Guidance literature:

With L-alanin; In water; at 130 ℃; for 5h; pH=5.0; Time; Sealed tube;

DOI:10.1021/acs.jafc.7b04105

Reference yield:

D-maltose (69-79-4) → furfural (98-01-1) + 1-(2-furyl)-1-ethanone (1192-62-7,80145-44-4) + 5-hydroxymethyl-2-furfuraldehyde (67-47-0) + Maltol (118-71-8) + D-Fructose (57-48-7,18875-34-8) + 2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one (28564-83-2) + D-glucose (50-99-7) + D-glucosone (643-71-0,25990-59-4,26187-86-0,26345-59-5,49865-02-3,54142-77-7,81844-97-5,81844-98-6,81845-00-3,89576-70-5,90457-64-0,1854-25-7) + 3-deoxygalactosone (4084-27-9,30382-30-0,50455-94-2,82399-12-0,4134-97-8) + 3-deoxyglucosone (4134-97-8,30382-30-0,50455-94-2,82399-12-0,4084-27-9) + 1-deoxymaltosone + 3-deoxymaltosone + 3-deoxypentos-2-ulose + 1,4-dideoxyhexosulose

Guidance literature:

With L-alanin; In water; at 130 ℃; for 5h; pH=5.0; Time; Sealed tube;

DOI:10.1021/acs.jafc.7b04105

upstream raw materials:

D-Fructose

glucose

glucosazone

D-arabino-[2]hexosulose-bis-(methyl-phenyl-hydrazone)

Downstream raw materials:

lyxo-[2]Hexosulose-bis-phenylhydrazon

fructonic acid

D-glucoascorbic acid

L-guloascorbic acid

Refernces

• 1、 Qi, Yajing,Zhang, Hui,Zhang, Hao,Wu, Gangcheng,Wang, Li,Qian, Haifeng,Qi, Xiguang. "Epicatechin Adducting with 5-Hydroxymethylfurfural as an Inhibitory Mechanism against Acrylamide Formation in Maillard Reactions". . p. 12536 - 12543. Retrieved 2018/11/25.
• 2、 Liu, Zhifen,Lv, Yue,An, Zesheng. "Enzymatic Cascade Catalysis for the Synthesis of Multiblock and Ultrahigh-Molecular-Weight Polymers with Oxygen Tolerance". supporting information. p. 13852 - 13856. Retrieved 2017/10/09.