(2R,3s,4S)-pentane-1,2,3,4,5-pentol

• ChemBase ID: 73212
• Molecular Formular: C5H12O5
• Molecular Mass: 152.14578
• Monoisotopic Mass: 152.06847348
• SMILES: OC[C@H]([C@H]([C@H](CO)O)O)O
• Canonical SMILES: OC[C@H]([C@H]([C@H](CO)O)O)O
• InChI: InChI=1S/C5H12O5/c6-1-3(8)5(10)4(9)2-7/h3-10H,1-2H2/t3-,4+,5-
• InChIKey: HEBKCHPVOIAQTA-ZXFHETKHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3s,4S)-pentane-1,2,3,4,5-pentol
• IUPAC Traditional name: ribitol
• Synonyms: Adonitol; Adonite ); Ribitol; Adonite; Ribitol; Adonitol; Adonit; Adonitt; Adonitot; Adonitrot; Pentitot; 1,2,3,4,5-Pentanepentot; 1,2,3,4,5-Pentanot; (2R,3s,4S)-Pentane-1,2,3,4,5-pentot; Pentane-1,2,3,4,5-pentol; ADONITOL

Database IDs

• CAS Number: 488-81-3
• EC Number: 207-685-7
• MDL Number: MFCD00064291
• Beilstein Number: 1720524
• PubChem SID: 162038132; 24890979
• PubChem CID: 827; 6912
• CHEBI ID: 15963
• Chemspider ID: 10254628
• KEGG ID: C00474
• Wikipedia Title: Ribitol

CALCULATED PROPERTIES

• Acid pKa: 12.760078
• H Acceptors: 5
• H Donor: 5
• LogD (pH = 5.5): -3.099684
• LogD (pH = 7.4): -3.099686
• Log P: -3.099684
• Molar Refractivity: 32.4411 cm^3
• Polarizability: 13.261178 Å^3
• Polar Surface Area: 101.15 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 102°C

Safety Information

• Storage Condition: -20°C
• RTECS: VJ0800000
• German water hazard class: 3
• Risk Statements: —
• Safety Statements: S22 S24/25
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ≥99%
• Salt Data: Free Base
• Suitability: suitable for cell culture
• Quality Level: PREMIUM
• Product Line: BioReagent
• Empirical Formula (Hill Notation): C5H12O5

DETAILS

MP Biomedicals - 05206419

MP Biomedicals Rare Chemical collection

Selleck Chemicals - S2612

Research Area: Metabolic Disease
Biological Activity:
Ribitol (Adonitol) is a sugar alcohol formed by the reduction of ribose. Ribitol (Adonitol) is a crystalline pentose alcohol. Ribitol (Adonitol) occurs naturally in the plant Adonis vernalis, as well as in the cell walls of Gram positive bacteria (specifically, as ribitol phosphate, in teichoic acids).Ribitol (Adonitol) also contributes to the chemical structure of riboflavin. [1][2]

Sigma Aldrich - A9790

Application
Useful for studies of the thermo-tolerance of cells in cell culture.

Sigma Aldrich - A5502

Packaging
10 mg in autosmp vl
Application
Adonitol (Ribitol), a pentose alcohol, 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.

REFERENCES

• Foster G et al. Vet Microbiol. 2010 Aug 26;144(3-4):484-6.