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Eicosanoid


DATA No : XPR8026 INFORMANT : Yasuji Yamada

NAME : methyl (5S,6R,7Z)-7-[(2S)-2-acetoxy-4-chloro-2-[(2Z)-2-octenyl]-5-oxo-3-cyclopentenylidene]-5,6-diacetoxyheptanoate

COMMON NAME: Z-punaglandin 4 acetate
SYMBOL:
FORMULA: C27H35ClO9 MOL.WT (average) : 539.014


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BIOLOGICAL ACTIVITY

PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:[a]D+11deg(c 1.8, CHCl3) (Ref. 8036/8037)

DENSITY:

SOLUBILITY:
SPECTRAL DATA
UV SPECTRA:lmax (MeOH)254 nm(e6700), 241 nm(e5100) (Ref. 8036/8037)

IR SPECTRA:

NMR SPECTRA:1H-NMR(300MHz, CDCl3)dppm 0.87(3H, t, J=6.1Hz), 1.3(6H, m), 1.6(4H, m), 1.9(2H, m), 2.00(3H, s), 2.02(3H, s), 2.10(3H, s), 2.3(2H, m), 2.58(1H, dd), 2.86(1H, dd), 3.64(3H, s), 5.2(1H, m), 5.2(1H, m), 5.54(1H, dt, J=8.8, 10.7Hz), 6.09(1H, d), 6.46(1H, dd, J=3.9, 7.8Hz), 7.53(1H, s). (Ref. 8036/8037)13C-NMR(75MHz, CDCl3)dppm 14.0, 20.6, 20.8, 21.6, 22.6, 23.1, 27.5, 29.0, 30.0, 31.5, 33.5, 35.4, 51.6, 69.8, 74.0, 82.3, 120.6, 135.7, 135.8, 136.5, 142.5, 149.0, 173.1, 173.4, 173.7, 176.3, 190.8. (Ref. 8036/8037)

MASS SPECTRA:EIMS(70 eV)m/z 540(3.2), 480(0.9), 438(2.7), 429(2.6), 420(3.5), 387(18.6), 378(17.2), 360(14.1), 327(27.9), 308(20.4), 285(14.9), 43(100). (Ref. 8036/8037)

OTHER SPECTRA:
CHROMATOGRAM DATA

SOURCE
Punaglandins were isolated from a telestacean octocoral, Telesto riisei.(Ref. 8029/8036/8037)
CHEMICAL SYNTHESIS

METABOLISM

GENETIC INFORMATION

NOTE

REFERENCES
[8029]
AUTHOR:Baker,B.J., Okuda,R.K., Yu,P.T.K., and Scheuer, P.J.
TITLE:Punaglandins: Halogenated Antitumor Eicosanoids from the Octocoral Telesto riisei.
JOURNAL:J. Am. Chem. Soc.
VOL:107 PAGE : 2976 -2977 (1985)
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[8036]
AUTHOR:Baker, B. J., and Scheuer, P. J.
TITLE:The punaglandins: 10-chloroprostanoids from the octocoral Telesto riisei PubMed ID:7857405
JOURNAL:J Nat Prod.
VOL:57 PAGE : 1346-1353 (1994)
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[8037]
AUTHOR:Scheuer.P.J.
TITLE:Marine Natural Products Research: A Look into the Dive Bag.
JOURNAL:J. Nat.Prod.
VOL:58 PAGE : 335 -343 (1995)
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Last updated June 19, 2007. Copyright © 1989-2007 Japanese Conference on the Biochemistry of Lipids (JCBL). All rights reserved.