ChemicalBook--->CAS DataBase List--->23918-98-1

23918-98-1

23918-98-1 Structure

23918-98-1 Structure
IdentificationBack Directory
[Name]

4-(9-ADENYL)-D-ERYTHRO-2,3-DIHYDROXYBUTYRIC ACID
[CAS]

23918-98-1
[Synonyms]

AA-307
Lentysine
lentinacin
eritadenine
D-ERITADENINE
d-erythronicaci
4-(6-AMinopurin-9-yl)-4-deoxy-D-erythronic Acid
4-(9-ADENYL)-D-ERYTHRO-2,3-DIHYDROXYBUTYRIC ACID
d-4-(6-amino-9h-purin-9-yl)-4-deoxyerythronicacid
4-(6-AMino-9H-purin-9-yl)-4-deoxy-D-erythronic Acid
(αR,βR)-6-Amino-α,β-dihydroxy-9H-purine-9-butanoic acid
9H-Purine-9-butanoic acid, 6-amino-α,β-dihydroxy-, (αR,βR)-
Lentysine 4-(9-Adenyl)-D-erythro-2,3-dihydroxybutyric acid
6-amino-alpha,beta-dihydroxy-,(r-(r*,r*))-9h-purine-9-butanoicaci
[R-(R*,R*)]-6-Amino-alpha,beta-dihydroxy-9H-furine-9-butanoic acid
[Molecular Formula]

C9H11N5O4
[MDL Number]

MFCD01752730
[MOL File]

23918-98-1.mol
[Molecular Weight]

253.22
Chemical PropertiesBack Directory
[Melting point ]

>270°C (dec.)
[alpha ]

D +51.4° (c = 1.6 in 0.1N NaOH)
[Boiling point ]

721℃
[density ]

1.92
[refractive index ]

1.7610 (estimate)
[Fp ]

390℃
[storage temp. ]

Refrigerator
[solubility ]

Aqueous Acid (Slightly, Heated), DMSO (Slightly)
[form ]

Solid
[color ]

White to Light Beige
Hazard InformationBack Directory
[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.
[storage]

Store at -20°C
[References]

Chibata et al., Experientia, 25,1237 (1969)
Kamiya et al., Tetrahedron Lett., 4729 (1969)
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