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Steroid


DATA No : SST0009 INFORMANT : Hideaki Nishino

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

COMMON NAME: a-Ecdysone
SYMBOL:
FORMULA: C27H44O6 MOL.WT (average) : 464.635


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BIOLOGICAL ACTIVITY
Molting hormone of insects. (Ref. 0065/0066/0068/0069/0075)
PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:238-239degC (Ref. 0067/0068)

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:[a]20/578 = +62deg (Ref. 0067)

DENSITY:

SOLUBILITY:Sol in ethanol. (Ref. 0065)
SPECTRAL DATA
UV SPECTRA:max. 243nm (e=11,600), 293nm (e=15,800) (Ref. 0065/0068)

IR SPECTRA:KBr (/cm): 1658, 1652 (Ref. 0069)

NMR SPECTRA:n max. 73(18-H), 107(19-H), 124 and 131(21-H), 138(26-H and 27-H) cps (Ref. 0070)

MASS SPECTRA:m/e (t-190deg): 446(3%), 428(29), 418(2), 413(2), 410(3), 372(3), 359(4), 348(8), 330(15), 315(18), 300(23), 279(17), 267(5), 255(8),250(13), 249(10), 99(100), 81(61) (Ref. 0071)

OTHER SPECTRA:
CHROMATOGRAM DATA

SOURCE
Silkworm (Bombyx mori) (Ref. 0072) Rhizomes (Polypodium vulgare L.). (Ref. 0073) Bracken (Pteridium aquilium L.) (Ref. 0074)
CHEMICAL SYNTHESIS
Synthesis from stigma-22-ene-3,6-dione by dividing three partial structure, A-ring, B, C-ring, and side chain. (Ref. 0068) Synthesis from 3b-hydroxy-23,24-bisnorchol-5-en-22-oic acid, readily available starting material. (Ref. 0070) Synthesis from (20S)-2b,3b-diacetoxy-20-formyl-5b-pregn-7-en-6-one by Grinard reaction with 2-methyl-3-butyn-2-oltetrahydropyran-2-yl ether, followed by hydrogenation of the triple bond, removal of the protecting groups, and hydroxylation in 14a-position. (Ref. 0071) Synthesis from methyl 14a-hydroxy-2b,3b-isopropylidenedioxy-6-oxo-22,23-bisnor-5b-chol-7-enoate. (Ref. 0074)
METABOLISM

GENETIC INFORMATION

NOTE

REFERENCES
[0065]
AUTHOR:Karlson, P., Hoffmeister, H., Hummel, H., Hocks, P., and Spiteller, G.
TITLE:[On the chemistry of ecdysone. VI. Reactions of ecdysone molecules] PubMed ID:5849855
JOURNAL:Chem Ber.
VOL:98 PAGE : 2394-2402 (1965)
[TOP]

[0066]
AUTHOR:Huber, R., and Hoppe, W.
TITLE:[On the chemistry of ecdysone. VII. Analysis of the crystal and molecular structure of the molting hormone in insects, ecdysone, using the automized folding molecule method] PubMed ID:5849856
JOURNAL:Chem Ber.
VOL:98 PAGE : 2403-2424 (1965)
[TOP]

[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 : - ()
[TOP]

[0068]
AUTHOR:Mori,H., Shibata,K., Tsuneda,K., and Sawai,M.
TITLE:Synthesis of Ecdysone.
JOURNAL:Chem.Pharm.Bull.
VOL:16 PAGE : 563 -566 (1968)
[TOP]

[0069]
AUTHOR:Kaplanis, J. N., Thompson, M. J., Robbins, W. E., and Bryce, B. M.
TITLE:Insect hormones: alpha ecdysone and 20-hydroxyecdysone in bracken fern PubMed ID:6037858
JOURNAL:Science.
VOL:157 PAGE : 1436-1438 (1967)
[TOP]

[0070]
AUTHOR:Siddall, J. B., Marshall, J. P., Bowers, A., Cross, A. D., Edwards, J. A., and Fried, J. H.
TITLE:Synthetic studies on insect hormones. I. Synthesis of the tetracyclic nucleus of ecdysone PubMed ID:5900550
JOURNAL:J Am Chem Soc.
VOL:88 PAGE : 379-380 (1966)
[TOP]

[0071]
AUTHOR:Kerb, U., Schulz, G., Hocks, P., Wiechert, R., Furlenmeier, A., Furst, A., Langemann, A., and Waldvogel, G.
TITLE:[On the synthesis of ecdysone. IV. On insect hormones. The synthesis of the natural skin shedding hormone] PubMed ID:5924992
JOURNAL:Helv Chim Acta.
VOL:49 PAGE : 1601-1606 (1966)
[TOP]

[0072]
AUTHOR:Butenandt,A., and Karlson,P.
TITLE:Über die Isolierung eines Metamorphose-Hormons der Insekten in Kristallisierter Form.
JOURNAL:Z.Natureforsch
VOL:9 PAGE : 389 -391 (1954)
[TOP]

[0073]
AUTHOR:Heinrich, G., and Hoffmeister, H.
TITLE:[Ecdysone as companion substance of ecdysterone in Polypodium vulgare L] PubMed ID:6077902
JOURNAL:Experientia.
VOL:23 PAGE : 995- (1967)
[TOP]

[0074]
AUTHOR:Iddall, J. B., Cross, A. D., and Fried, J. H.
TITLE:Steroids. CCXCII. Synthetic studies on insect hormones. II. The synthesis of ecdysone PubMed ID:5902567
JOURNAL:J Am Chem Soc.
VOL:88 PAGE : 862-863 (1966)
[TOP]

[0075]
AUTHOR:Ashburner, M.
TITLE:Chromosomal action of ecdysone PubMed ID:6250033
JOURNAL:Nature.
VOL:285 PAGE : 435-436 (1980)
[TOP]

Last updated June 19, 2007. Copyright © 1989-2007 Japanese Conference on the Biochemistry of Lipids (JCBL). All rights reserved.