Title: Sakuranetin
CAS Registry Number: 2957-21-3
CAS Name: 2,3-Dihydro-5-hydroxy-2-(4-hydroxyphenyl)-7-methoxy-4H-1-benzopyran-4-one
Additional Names: 4¢,5-dihydroxy-7-methoxyflavanone; naringen 7-methyl ether
Molecular Formula: C16H14O5
Molecular Weight: 286.28
Percent Composition: C 67.13%, H 4.93%, O 27.94%
Literature References: Isoln by hydrolysis of 5-glucoside obtained from bark of Prunus yedoensis Matsum., Rosaceae: Asahina, Arch. Pharm. 246, 259 (1908); from wood of various Prunus species: Hasegawa, Shirato, J. Am. Chem. Soc. 76, 5559 (1954); 77, 3557 (1955); Hasegawa, ibid. 79, 1738 (1957). Structure: Asahina et al., J. Pharm. Soc. Jpn. No. 550, 1007 (1927); Shinoda, Sato, ibid. 48, 220 (1928). Synthesis: Zemplén et al., Ber. 75B, 1432 (1942). Absolute configuration of (+)-isomer: Arakawa, Nakazaki, Ann. 636, 111 (1960).
Properties: Needles, mp 152°. Also reported as dihydrate, mp 131-132° (Arakawa, Nakazaki, loc. cit.). (+)-Isomer, [a]D16 +8.0° (c = 7.92 in acetone); [a]D12 +8.4° (c = 6.28 in methanol). Sol in alcohol, ether, chloroform, benzene, ethyl acetate, pyridine; slightly sol in boiling water. Practically insol in cold water.
Melting point: mp 152°; mp 131-132° (Arakawa, Nakazaki, loc. cit.)
Optical Rotation: [a]D16 +8.0° (c = 7.92 in acetone); [a]D12 +8.4° (c = 6.28 in methanol)
Derivative Type: 5-Glucoside
Additional Names: 4¢,5-dihydroxy-7-methoxyflavanone 5-glucoside; sakuranin
Molecular Formula: C22H24O10
Molecular Weight: 448.42
Percent Composition: C 58.93%, H 5.39%, O 35.68%
Properties: Tetrahydrate, bitter needles from dil alcohol. Begins to lose water at 100°. mp 212-214°. [a]D28 -106.6° (tetrahydrate in acetone); [a]D28 -123.2° (anhydr compd in acetone); [a]D16 -97.4° (c = 1.58 for anhydr compd in 75% acetone). Very sol in dil alcohol, pyridine; slightly sol in abs alcohol, hot water, ethyl acetate. Practically insol in ether, cold water.
Melting point: mp 212-214°
Optical Rotation: [a]D28 -106.6° (tetrahydrate in acetone); [a]D28 -123.2° (anhydr compd in acetone); [a]D16 -97.4° (c = 1.58 for anhydr compd in 75% acetone)
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