2-Deoxy-D-ribose Chemical Properties

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 Information

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

MSDS

• Language:English Provider:2-Deoxy-D-arabinose
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

2-Deoxy-D-ribose Usage And Synthesis

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.

Uses

2-Deoxy-D-ribose (2dDR) can be used to prepare multifunctional wound dressings capable of inducing rapid angiogenesis with antimicrobial activity, such as 2dDR-SA hydrogel. The gel can be used to stimulate wound healing and treat superficial skin wounds, including chronic wound care. In addition, 2dDR gel has the potential to treat androgenetic alopecia and other causes of alopecia areata.

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.

benefits

Hair Regrowth in Mice: Applying a small dose of 2-deoxy-D-ribose to mice models led to significant hair regrowth.
Blood Vessel Formation: The hair regrowth was linked to forming new blood vessels, enhancing blood supply to hair follicles.
Comparable to Minoxidil: The effectiveness of 2-deoxy-D-ribose in regrowing hair was similar to that of Minoxidil, a widely used hair loss treatment.

Biological Activity

2-Deoxy-D-ribose (2dDR) is a D-isomer of a deoxypentose monosaccharide in which a hydrogen atom is present with a hydroxyl group at the C-2 position in place of the hydroxyl group. 2dDR is known to enhance tubulogenesis, prevent hypoxia-induced apoptosis, and boost VEGF and IL-8 production of ECs in vitro, consistent with the stimulatory effects of 2dDR on cell proliferation and migration. 2dDR also stimulated angiogenesis, proliferation of endothelial cells, and accelerated wound healing in rat models. Additionally, 2dDR can be loaded into several biomaterials for prolonged release over several days to promote the growth of neonatal blood vessels[1].

References

[1] Anjum, Muhammad Awais et al. “Stimulation of hair regrowth in an animal model of androgenic alopecia using 2-deoxy-D-ribose.” Frontiers in Pharmacology 44 16 (2024).

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