533-67-5

2-deoxy-D-Ribose (CAS: 533-67-5) is a reducing sugar formed as a degradation product during metabolism of thymidine (Item No. 20519) 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.

White powder

2-Deoxy-D-ribose(533-67-5) induces apoptosis by inhibiting the synthesis and increasing the efflux of glutathione.

ChEBI: A deoxypentose that is D-ribose in which the hydroxy group at position C-2 is replaced by hydrogen.

Hair Regrowth in Mice: Applying a small dose of 2-deoxy-D-ribose(533-67-5) 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.

2-Deoxy-D-ribose (2dDR,533-67-5) 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].

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.]

[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).