2-Deoxy-D-ribose Property

Melting point:

89-90 °C(lit.)

alpha 

-57 º (c=1, H2O, 24hr)

Boiling point:

167.23°C (rough estimate)

Density 

1.0590 (rough estimate)

refractive index 

-56 ° (C=1, H2O)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

solubility 

DMSO (Slightly), Methanol (Slightly), Water (Slightly, Sonicated)

form 

Crystalline Powder

pka

12.61(at 25℃)

color 

White to slightly yellow

optical activity

[α]22/D 59°, c = 1 in H2O

Water Solubility 

soluble

Sensitive 

Hygroscopic

Merck 

14,2908

BRN 

1721978

Stability:

Hygroscopic

InChIKey

ASJSAQIRZKANQN-CRCLSJGQSA-N

CAS DataBase Reference

533-67-5(CAS DataBase Reference)

NIST Chemistry Reference

D-Erythro-pentose, 2-deoxy-(533-67-5)

EPA Substance Registry System

D-erythro-Pentose, 2-deoxy- (533-67-5)

Safety

Hazard Codes 

Xn,Xi

Risk Statements 

20/21/22-36/37/38

Safety Statements 

24/25-37/39-36-26

WGK Germany 

3

RTECS 

SB7230000

F 

3-10

TSCA 

Yes

HS Code 

29400000

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H332Harmful if inhaled

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

2-Deoxy-D-ribose Chemical Properties,Usage,Production

Description

2-deoxy-D-Ribose is a reducing sugar formed as a degradation product during metabolism of thymidine by thymidine phosphorylase. It increases levels of reactive oxygen species (ROS) in HL-60 human leukemia cells when used at a concentration of 15 mM. 2-deoxy-D-Ribose (10 μM) induces tubulogenesis and migration of bovine aortic endothelial (BAE) cells. Topical administration of 2-deoxy-D-ribose increases blood vessel formation and accelerates wound healing in a rat full-thickness cutaneous wound model.

Chemical Properties

White powder

Uses

2-Deoxy-D-ribose is used as a precursor to deoxyribonucleic acid. It induces apoptosis by inhibiting the synthesis and increasing the efflux of glutathione. Further, it is used in the synthesis of optically active dipyrrolyl alkanols from pyrroles on the surface of montmorillonite KSF clay.

Definition

ChEBI: 2-deoxy-D-ribose is a deoxypentose that is D-ribose in which the hydroxy group at position C-2 is replaced by hydrogen. It has a role as a human metabolite, a Saccharomyces cerevisiae metabolite and a mouse metabolite. It is functionally related to a D-ribose.

Purification Methods

Dissolve 2-deoxy--D-ribose in a little H2O, evaporate to a syrup (in a vacuum), and seed to crystallise. Triturate the crystals with a little EtOAc containing 5% MeOH, decant and dry in vacuum over P2O5. It is best purified via the anilide which separates from a mixture of the ribose (100-125g) in MeOH (100mL) and redistilled aniline (40mL) in a few minutes. After standing for 20hours at room temperature, it is cooled to 0o, filtered, washed with 50% aqueous MeOH and Et2O followed by recrystallisation from ethylene glycol monomethyl ether. The anilide has m 172-173o, [ ] D 25 +46o (equilibrium in pyridine). The anilide (5g), benzaldehyde (5mL) and benzoic acid (0.5g) in H2O (150mL) are shaken mechanically for 2024hours. The aqueous phase is extracted with Et2O (3x), decolourised with a little charcoal and evaporated in a vacuum to a syrup. This is dried over P2O5 in high vacuum. The syrupy sugar weighs 3.1g and crystallises in a few days, but more rapidly on seeding. Triturate it with a little EtOAc containing 5% MeOH, decant and dry it over P2O5. At this stage it has m 78-82o, [ ] D 25 -57o (c 1, H2O final). This is a mixture of and anomers. Pure -anomer is obtained by recrystallisation from EtOAc The -anomer when recrystallised from EtOAc and isoPrOH has m 96-98o, [ ] D 25 -55o (c 0.5, H2O final). [Sowden Biochemical Preparations 5 75 1957.] The mutarotation is as follows: [] D 20.5 +96.3o(0minutes), -76o(33minutes), -56o (24hours) (c 5.8 MeOH). It is moderately hygroscopic and should be kept in a well stoppered bottle. It also crystallises from diethyl ether. [Deriaz et al. J Chem Soc 1879 1949, Beilstein 1 IV 4181, Hauske & Rapoport J Org Chem 4 4 2472 1979.]