| Identification | More | [Name]
2-Deoxy-D-ribose | [CAS]
533-67-5 | [Synonyms]
2-DEOXY-D-ARABINOSE
2-DEOXY-D-ERYTHRO-PENTOSE
2'-DEOXY-D-RIBOSE
2-DEOXY-D-RIBOSE
2-DEOXYRIBOSE
2-DESOXY-D-RIBOSE
D-(-)-2-DEOXYRIBOSE
D-2-DEOXYRIBOSE
D-2-DESOXYRIBOSE
DEOXY-D-RIBOSE,2-
D-ERYTHRO-2-DEOXYPENTOSE
TETRAHYDRO-2H-PYRAN-2,4,5-TRIOL
THYMINOSE
.alpha.-Deoxy-D-ribose
2-deoxy-d-erythro-pentos
2-Deoxypentose
2-Desoxy ribosoe
D-.alpha.-Ribodesose
Deoxyribose
D-Ribose, 2-deoxy- | [EINECS(EC#)]
208-573-0 | [Molecular Formula]
C5H10O4 | [MDL Number]
MFCD00135904 | [Molecular Weight]
134.13 | [MOL File]
533-67-5.mol |
| Chemical Properties | Back Directory | [Appearance]
White powder | [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. ]
2-8°C
| [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]
533-67-5(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
Xn,Xi | [Risk Statements ]
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed .
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S24/25:Avoid contact with skin and eyes .
S37/39:Wear suitable gloves and eye/face protection .
S36:Wear suitable protective clothing .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice . | [WGK Germany ]
3
| [RTECS ]
SB7230000
| [F ]
3-10 | [TSCA ]
Yes | [HS Code ]
29400000 |
| Hazard Information | Back Directory | [Description]
2-deoxy-D-Ribose is a reducing sugar formed as a degradation product during metabolism of thymidine (Item No. 20519) by thymidine phosphorylase.1 It increases levels of reactive oxygen species (ROS) in HL-60 human leukemia cells when used at a concentration of 15 mM.2 2-deoxy-D-Ribose (10 μM) induces tubulogenesis and migration of bovine aortic endothelial (BAE) cells.3 Topical administration of 2-deoxy-D-ribose increases blood vessel formation and accelerates wound healing in a rat full-thickness cutaneous wound model.4 | [Chemical Properties]
White powder | [Uses]
2-Deoxy-D-ribose induces apoptosis by inhibiting the synthesis and increasing the efflux of glutathione. | [Definition]
ChEBI: A deoxypentose that is D-ribose in which the hydroxy group at position C-2 is replaced by hydrogen. | [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.] |
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