4-(9-ADENYL)-D-ERYTHRO-2,3-DIHYDROXYBUTYRIC ACID
4-(9-ADENYL)-D-ERYTHRO-2,3-DIHYDROXYBUTYRIC ACID Basic information
- Product Name:
- 4-(9-ADENYL)-D-ERYTHRO-2,3-DIHYDROXYBUTYRIC ACID
- Synonyms:
-
- 4-(9-ADENYL)-D-ERYTHRO-2,3-DIHYDROXYBUTYRIC ACID
- 6-amino-alpha,beta-dihydroxy-,(r-(r*,r*))-9h-purine-9-butanoicaci
- d-4-(6-amino-9h-purin-9-yl)-4-deoxyerythronicacid
- d-erythronicaci
- eritadenine
- lentinacin
- D-ERITADENINE
- (αR,βR)-6-Amino-α,β-dihydroxy-9H-purine-9-butanoic acid
- CAS:
- 23918-98-1
- MF:
- C9H11N5O4
- MW:
- 253.22
- Product Categories:
-
- Inhibitors
- Intermediates & Fine Chemicals
- Pharmaceuticals
- A potent inhibitor of S-adenosyl-L-homocysteine hydrolase.
- Mol File:
- 23918-98-1.mol
4-(9-ADENYL)-D-ERYTHRO-2,3-DIHYDROXYBUTYRIC ACID Chemical Properties
- Melting point:
- >270°C (dec.)
- Boiling point:
- 721℃
- alpha
- D +51.4° (c = 1.6 in 0.1N NaOH)
- Density
- 1.92
- refractive index
- 1.7610 (estimate)
- Flash point:
- 390℃
- storage temp.
- Refrigerator
- solubility
- Aqueous Acid (Slightly, Heated), DMSO (Slightly)
- form
- Solid
- pka
- 3.37±0.17(Predicted)
- color
- White to Light Beige
4-(9-ADENYL)-D-ERYTHRO-2,3-DIHYDROXYBUTYRIC ACID Usage And Synthesis
Description
The empirical formula of this alkaloid should read C9H II N 504' The natural compound is the D-Erythro-form of the base. Melting points recorded for this alkaloid are 279°C (dec.) by Kamiya et al and 26l-3°C (dec.) by Chibata and his colleagues. The alkaloid has specific rotations of [α]D+ 16° (N-HC1) and [α] D + 50° (0.1 N-NaOH). It gives an ultraviolet spectrum in H20 with a single absorption maximum at 26l.5 nm which is shifted to 259.5 nm inN-HCl and is at 262 nm in N-NaOH. Eritadenine forms a methyl ester, m.p. 231°C (dec.) and a diacetate, m.p. 225°C (dec.).
Chemical Properties
Pale Yellow Solid
Uses
Hypocholesterolemic isolated from shiitake mushrooms, effecting phospholipid and linoleic acid metabolisms. Specifically, Eritadenine is a potent inhibitor of S-adenosyl-L-homocysteine hydrolase (SAHH), decreasing total cholesterol levels in plasma.
References
Chibata et al., Experientia, 25,1237 (1969)
Kamiya et al., Tetrahedron Lett., 4729 (1969)
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