2-Deoxy-D-ribose Basic information |
Product Name: | 2-Deoxy-D-ribose |
Synonyms: | D-.alpha.-Ribodesose;Deoxyribose;D-Ribose, 2-deoxy-;2-deoxy-d-erythro-pentos;2-Deoxypentose;2-Desoxy ribosoe;D-(-)-2-DEOXYRIBOSE;D-2-DEOXYRIBOSE |
CAS: | 533-67-5 |
MF: | C5H10O4 |
MW: | 134.13 |
EINECS: | 208-573-0 |
Product Categories: | FINE Chemical & INTERMEDIATES;Pharmaceutical Raw Materials;13C & 2H Sugars;Riboses and 2'-Deoxyriboses;Biochemistry;Deoxysugars;Nucleosides, Nucleotides & Related Reagents;Ribose;Sugars;Dextrins,Sugar & Carbohydrates;aldehydes;Carbohydrates & Derivatives;nucleoside |
Mol File: | 533-67-5.mol |
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. | 2-8°C |
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 |
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 Information |
Provider | Language |
---|---|
2-Deoxy-D-arabinose | English |
ACROS | English |
SigmaAldrich | English |
ALFA | English |
2-Deoxy-D-ribose Usage And Synthesis |
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 r. 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 r. [Deriaz et al. J Chem Soc 1879 1949, Beilstein 1 IV 4181, Hauske & Rapoport J Org Chem 4 4 2472 1979.] |