Steroid

DATA No : SST0010 INFORMANT : Hideaki Nishino

NAME : 2,3,14,20,22,25-Hexahydroxycholest-7-en-6-one

COMMON NAME	:	b-Ecdysone / 20-Hydroxyecdysone / Ecdysterone / Crustecdysone / Isoinokosterone
SYMBOL	:
FORMULA	:	C₂₇H₄₄O₇ MOL.WT (average) : 480.634

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BIOLOGICAL ACTIVITY

Molting and metamorphosis hormone for Insecta and Crustacea. Much potent than a-ecdysone. (Ref. 0077)

PHYSICAL AND CHEMICAL PROPERTIES

MELTING POINT	:	240-242C (methanol-ethylacetate) (Ref. 0079)

BOILING POINT	:

REFRACTIVE INDEX	:

OPTICAL ROTATION	:	[a]28/D = +63(c=1.0, methanol) (Ref. 0080)

DENSITY	:

SOLUBILITY	:	Sol in methanol, ethanol. (Ref. 0080)

SPECTRAL DATA

UV SPECTRA	:	max. 243nm (e= 10,300), 240nm (ethanol, e= 12,670), 242nm (methanol, e= 12,400) (Ref. 0067/0079/0077)

IR SPECTRA	:	n KBr/max. 1656, 1615, 1387, 1229, 1053, 917, 878 /cm (Ref. 0079)

NMR SPECTRA	:	Pyridine-d₅: 1.07(19-H), 1.20(18-H), 1.36(26- and 27-H), 1.56(21-H), 6.17(7-H) (Ref. 0079)

MASS SPECTRA	:	m/e: 480 (ecdysone+0), 462 (M-H₂O), 444 (M-2H₂O), 426 (M-3H₂O), 408 (M-4H₂O) (Ref. 0077)

OTHER SPECTRA	:

CHROMATOGRAM DATA

SOURCE

Silkworm (Bombyx mori) (Ref. 0077) Crawfish (crayfish) (Jasus lalandei) (Ref. 0078) Achyranthis radix (as phytoecdysone) (Ref. 0080) Australia timber tree (Podocarpus elatus) (Ref. 0081) Lemmaphyllum microphyllum, Trillium smallii (Ref. 0082)

CHEMICAL SYNTHESIS

Synthesis from hydroxylated aldehyde precursor, (20S)-2b,3b-diacetoxy-5a-hydroxy-20-methoxycarbonylpregn-7-en-6-one. (Ref. 0079) Synthesis from 20b-hydroxy-5a-pregnane-3,6-dione via 2b,3b-diacetoxy-5a-pregn-7-ene-6,20-dione. (Ref. 0083) Stereospecific synthesis from 20bbenzoyloxy-5-pregnen-3b-ol. (Ref. 0084) Stereocontrolled total synthesis from 2b,3b,20b,-triacetoxy-5a-pregnan 6-one via acetylene-cationcyclization. (Ref. 0085)

METABOLISM

GENETIC INFORMATION

NOTE

The complete structure of natural b-ecdysone determined by a three-dimensional X-ray analysis using convolution molecule method. (Ref. 0076)

REFERENCES

[0067]

AUTHOR	:	Monographs in the Merck Index an encyclopedia of chemicals, drugs, and biologicals (Budavari,S., O'Neil,M.J., Smith,A., and Heckelman,P.E.,eds. 1989), pp547-547, MERCK & CO., Inc. Rahway, N.J.
TITLE	:
JOURNAL	:
VOL	:	PAGE : - ()

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[0076]

AUTHOR	:	Dammeier, B., and Hoppe, W.
TITLE	:	[The crystal and molecular structure analysis of the insectmoulting hormone 20-hydroxyecdysone (Ecdysterone)] PubMed ID:5154405
JOURNAL	:	Chem Ber.
VOL	:	104 PAGE : 1660-1673 (1971)

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[0077]

AUTHOR	:	Hocks,P., and Wiechert,R.
TITLE	:	20-Hydroxy-Ecdyson, Isoliert aus Insekten.
JOURNAL	:	Tetrahedron Lett.
VOL	:	1966 PAGE : 2989 -2993 (1966)

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[0078]

AUTHOR	:	Hampshire,F., and Horn,D.H.S.
TITLE	:	Structure of Crustecdysone, a Crustacean Moulting Hormone.
JOURNAL	:	J.Chem.Soc., Chem Commun.
VOL	:	1966 PAGE : 37 -38 (1966)

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[0079]

AUTHOR	:	Hüppi,G., and Siddall,J.B.
TITLE	:	Steroids. CCCXXXIII. Synthetic Studies on Insect Hormones. V. The Synthesis of Crustecdysone (20-Hydroxyecdysone).
JOURNAL	:	J.Am.Chem.Soc.
VOL	:	89 PAGE : 6790 -6792 (1967)

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[0080]

AUTHOR	:	Takemoto,T., Ogawa,S., and Nishimoto,N.
TITLE	:	Isolation of the Moulting Hormones of Insects from Achyranthis Radix.
JOURNAL	:	Yakugaku Zasshi
VOL	:	87 PAGE : 325 -327 (1967)

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[0081]

AUTHOR	:	Galbraith,M.N., and Horn,D.H.S.
TITLE	:	An Insect-Moulting Hormone from a Plant.
JOURNAL	:	J.Chem.Soc., Chem.Commun.
VOL	:	1966 PAGE : 905 -906 (1966)

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[0082]

AUTHOR	:	Horn, D. H., Fabbri, S., Hampshire, F., and Lowe, M. E.
TITLE	:	Isolation of crustecdysone (20R-hydroxyecdysone) from a crayfish (Jasus lalandei H. Milne-Edwards) PubMed ID:5685865
JOURNAL	:	Biochem J.
VOL	:	109 PAGE : 399-406 (1968)

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[0083]

AUTHOR	:	Kerb,U., Wiechert,R., Furlenmeier,A., and Fürst,A.
TITLE	:	Über eine Synthese des Crustecdysons (20-Hydroxyecdyson).
JOURNAL	:	Tetrahedron Lett.
VOL	:	1968 PAGE : 4277 -4280 (1968)

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[0084]

AUTHOR	:	Mori, H., and Shibata, K.
TITLE	:	Synthesis of ecdysterone PubMed ID:5347599
JOURNAL	:	Chem Pharm Bull (Tokyo).
VOL	:	17 PAGE : 1970-1973 (1969)

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[0085]

AUTHOR	:	Kametani,T., Tsubuki,M., and Nemoto,H.
TITLE	:	A Stereocontrolled Total Synthesis of 2b,3b,20b-Triacetoxy-5a-Pregnan-6-One. A Total Synthesis of 20-Hydroxyecdysone.
JOURNAL	:	Tetrahedron Lett.
VOL	:	21 PAGE : 4855 -4856 (1980)

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