2-Desoxy-D-ribose

Bezeichnung:2-Desoxy-D-ribose

CAS-Nr533-67-5

Englisch Name:2-Deoxy-D-ribose

CBNumberCB5315585

SummenformelC5H10O4

Molgewicht134.13

MOL-Datei533-67-5.mol

Synonyma

2-Desoxy-D-ribose

2-Desoxy-D-ribose physikalisch-chemischer Eigenschaften

Schmelzpunkt	89-90 °C(lit.)
Siedepunkt	167.23°C (rough estimate)
alpha	-57 º (c=1, H2O, 24hr)
Dichte	1.0590 (rough estimate)
Brechungsindex	-56 ° (C=1, H2O)
storage temp.	Keep in dark place,Inert atmosphere,Room temperature
Löslichkeit	DMSO (Slightly), Methanol (Slightly), Water (Slightly, Sonicated)
Aggregatzustand	Crystalline Powder
pka	12.61(at 25℃)
Farbe	White to slightly yellow
Optische Aktivität	[α]22/D 59°, c = 1 in H2O
Wasserlöslichkeit	soluble
Sensitive	Hygroscopic
Merck	14,2908
BRN	1721978
Stabilität	Hygroscopic
InChIKey	ASJSAQIRZKANQN-CRCLSJGQSA-N
CAS Datenbank	533-67-5(CAS DataBase Reference)
NIST chemische Informationen	D-Erythro-pentose, 2-deoxy-(533-67-5)
EPA chemische Informationen	D-erythro-Pentose, 2-deoxy- (533-67-5)

Sicherheit

Kennzeichnung gefährlicher	Xn,Xi
R-Sätze:	20/21/22-36/37/38
S-Sätze:	24/25-37/39-36-26
WGK Germany	3
RTECS-Nr.	SB7230000
F	3-10
TSCA	Yes
HS Code	29400000

Gefahreninformationscode (GHS)

2-Deoxy-D-ribose Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R20/21/22:Gesundheitsschädlich beim Einatmen,Verschlucken und Berührung mit der Haut.
R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.
S-Sätze Betriebsanweisung:
S24/25:Berührung mit den Augen und der Haut vermeiden.
S37/39:Bei der Arbeit geeignete Schutzhandschuhe und Schutzbrille/Gesichtsschutz tragen.
S36:DE: Bei der Arbeit geeignete Schutzkleidung tragen.
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
Beschreibung
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.
Chemische Eigenschaften
White powder
Verwenden
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.
läuterung methode
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.]

2-Deoxy-D-ribose Upstream-Materialien And Downstream Produkte

2-Desoxy-D-ribose Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

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