ADONITOL

Base Information

• Chemical Name: ADONITOL
• CAS No.: 488-81-3
• Deprecated CAS: 12426-00-5,37191-59-6,7313-55-5,75398-81-1,84709-42-2
• Molecular Formula: C5H12O5
• Molecular Weight: 152.147
• Hs Code.: 29054990
• NSC Number: 83253,25288,25283,16868
• DSSTox Substance ID: DTXSID7042514
• Nikkaji Number: J1.453.993J
• Wikidata: Q81977867
• Metabolomics Workbench ID: 123381
• ChEMBL ID: CHEMBL1369426
• Mol file: 488-81-3.mol

Synonyms:Adonitol(7CI);Adonit;Adonite;NSC 16868;ribo-Pentitol;Ribitol;

Chemical Property of ADONITOL

Chemical Property:

• Appearance/Colour: White powder
• Vapor Pressure: 7.47E-12mmHg at 25°C
• Melting Point: 102-105 °C
• Refractive Index: 1.57
• Boiling Point: 494.527 °C at 760 mmHg
• PKA: 13.24±0.20(Predicted)
• Flash Point: 261.85 °C
• PSA: 101.15000
• Density: 1.526 g/cm³
• LogP: -2.94630
• Storage Temp.: Store at RT.
• Sensitive.: Hygroscopic
• Water Solubility.: Soluble in water (100 mg/ml).
• XLogP3: -2.5
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 152.06847348
• Heavy Atom Count: 10
• Complexity: 76.1

Purity/Quality:

99%, ^*data from raw suppliers

Ribitol ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 24/25-36-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C(C(C(C(CO)O)O)O)O
• Uses: A sugar alcohol formed by the reduction of ribose Adonitol is metabolized to teicholic acids used in the cell walls of gram positive bacteria. Adonitol is often compared to other cell permeating molecules such as formamide, propanediol, and DMSO as a cryopreservation agent.

Technology Process of ADONITOL

There total 90 articles about ADONITOL 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:

α-cellulose → 1,4-sorbitan (20662-31-1) + β-D-glucose (492-61-5) + 1,2,3,4,5-pentahydroxy-pentane (87-99-0,488-81-3,488-82-4,2152-56-9,6917-36-8,7643-75-6) + sorbitol (50-70-4,69-65-8,87-78-5,133-43-7,488-44-8,488-45-9,608-66-2,643-01-6,643-03-8,5552-13-6,6706-59-8,24557-79-7,25878-23-3,26566-34-7,45007-61-2,60660-56-2,60660-57-3,60660-58-4,132747-27-4)

Guidance literature:

With sulfuric acid; 5% active carbon-supported ruthenium; water; hydrogen; tungsten; at 159.84 ℃; for 1h; under 37503.8 Torr; Autoclave;

DOI:10.1039/c0cc02263b

Reference yield:

cellulose (9004-34-6) → D-Arabitol (488-82-4) + XYLITOL (87-99-0) + Adonitol (488-81-3) + mannitol (69-65-8) + D-sorbitol (50-70-4) + ethylene glycol (107-21-1)

Guidance literature:

With Ru/C; hydrogen; In water; at 204.84 ℃; for 0.5h; under 45004.5 Torr; Autoclave;

DOI:10.1016/j.cattod.2015.09.056

Reference yield:

alginic acid (9005-32-7) → 1,2,3,4,5-pentapentanol (6018-27-5) + XYLITOL (87-99-0) + Adonitol (488-81-3) + mannitol (69-65-8) + D-sorbitol (50-70-4) + D-allono-1,4-lactone (29474-78-0) + D-Glucono-1,5-lactone (90-80-2,1335-57-5,4253-68-3)

Guidance literature:

With hydrogen; In water; at 180 ℃; under 37503.8 Torr; Reagent/catalyst; Autoclave;

DOI:10.1016/j.apcata.2019.04.003

upstream raw materials:

DL-erythro-pentene-⁽¹⁾-triol-(3.4.5)-triacetate

D-ribose

L-ribose

D-Fructose

Downstream raw materials:

D-ribulose

3-hydroxy-2-butanon

2.3-butanediol

1,4-anhydro-D,L-ribitol

Refernces

• 1、 Arbatsky, Nikolay P.,Kondakova, Anna N.,Senchenkova, Sof'ya N.,Siwinska, Malgorzata,Shashkov, Alexander S.,Zych, Krystyna,Knirel, Yuriy A.,Sidorczyk, Zygmunt. "Structure of a new ribitol teichoic acid-like O-polysaccharide of a serologically separate Proteus vulgaris strain, TG 276-1, classified into a new Proteus serogroup O53". . p. 2061 - 2066. Retrieved 2007.
• 2、 Fongarland, Pascal,Freitas, Victoria D. S.,Paez, Ana,Philippe, Régis,Veyre, Laurent,Vilcocq, Léa. "Unexpected reactivity related to support effects during xylose hydrogenation over ruthenium catalysts". . p. 39387 - 39398. Retrieved 2021/12/27.
• 3、 Ban, Chunghyeon,Yang, Seungdo,Kim, Hyungjoo,Kim, Do Heui. "Effect of Cu addition to carbon-supported Ru catalysts on hydrogenation of alginic acid into sugar alcohols". . p. 98 - 104. Retrieved 2019/04/17.