(2R,5R)-2,5-Hexanediol - CAS 17299-07-9

(2R,5R)-2,5-Hexanediol, a compound utilized in the manufacturing of pharmaceuticals and various biologically active substances, has garnered attention for its promising antimicrobial attributes. Ongoing research is exploring its efficacy in combatting infections induced by drug-resistant bacterial strains.

Catalog Number

17299-07-9

CAS

17299-07-9

IUPAC Name

(2R,5R)-hexane-2,5-diol

Synonyms

2,5-Hexanediol, (2R,5R)-; (2R,5R)-2,5-Dihydroxyhexane; (2R,5R)-hexanediol; 2,5-Hexanediol, (R,R)-; 2,5-Hexanediol, [R-(R*,R*)]-; (-)-2,5-Hexanediol; (2R,5R)-(-)-2,5-Hexanediol; (R,R)-2,5-Hexanediol

Molecular Weight

118.17

Molecular Formula

C6H14O2

Product Information

Canonical SMILES

CC(CCC(C)O)O

InChI

InChI=1S/C6H14O2/c1-5(7)3-4-6(2)8/h5-8H,3-4H2,1-2H3/t5-,6-/m1/s1

InChI Key

OHMBHFSEKCCCBW-PHDIDXHHSA-N

Purity

≥95%

MDL

MFCD00142339

Physical State

Solid

Appearance

White to Yellow Crystalline Powder or Needles

Storage

Store at 2-8°C

Boiling Point

213.4±8.0°C at 760 mmHg

Melting Point

52-53°C

Density

0.958±0.06 g/cm3

Optical Activity

-25° (c=1 in ethanol)

Solubility

Soluble in Methanol

WGK Germany

Safety Information

Signal Word

Warning

Precautionary Statement

P261 - P305+P351+P338

Hazard Statements

H302 - H315 - H319 - H335

Reference Reading

1. Diastereoselective synthesis of optically active (2 r,5 r)-hexanediol.

W Hummel, E Wolfram, A Liese, A Kriegesmann, J Haberland. Appl Microbiol Biotechnol. 2002 Apr; 58(5): 595-9. DOI: 10.1007/s00253-002-0936-5. PMID: 11956740.

Diastereoselective reduction of diketones with Lactobacillus kefir DSM 20587 was examined. The reduction of both oxo-functions proceeded highly diastereoselectively. (2 R,5 R)-Hexanediol 3 was produced starting from (2,5)-hexanedione 1 in quantitative yields with enantiomeric excess >99% and diastereomeric excess >99%. The reaction conditions were optimized: maximum yield of (2 R,5 R)-hexanediol was reached at pH 6, 30 degrees C and with equal amounts of substrate and cosubstrate. The applicability of the system in fed-batch experiments was demonstrated. The feed specific biomass concentration required to reach maximal yield and selectivity in fed-batch mode was determined.

The molarity calculator equation

Mass (g) = Concentration (mol/L) × Volume (L) × Molecular Weight (g/mol)

Mass