Balsaminapentaol or cucurbita-5,25-diene-3β,7β,23(R),24(R),29-pentaol, is a chemical compound with formula C
30
H
50
O
5
, found in the Balsam apple vine (Momordica balsamina). It is a cucurbitane-type triterpenoid, related to cucurbitacin, isolated by C. Ramalhete and others in 2009.[1]

Balsaminapentaol
Names
IUPAC name
(23R,24R)-9-Methyl-19-nor-9β,10α-lanosta-5,25-diene-3β,7β,23,24,29-pentol
Systematic IUPAC name
(1R,3aS,3bR,4S,6S,7S,9aS,9bS,11aR)-1-[(2R,4R,5R)-4,5-Dihydroxy-6-methylhept-6-en-2-yl]-6-(hydroxymethyl)-3a,6,9b,11a-tetramethyl-2,3,3a,3b,4,6,7,8,9,9a,9b,10,11,11a-tetradecahydro-1H-cyclopenta[a]phenanthrene-4,7-diol
Other names
Cucurbita-5,25-diene-3β,7β,23R,24R,29-pentaol; (3β,4β,7β,9β,10α,23R,24R)-4-(Hydroxymethyl)-4,9,14-trimethyl-19-norcholesta-5,25-diene-3,7,23,24-tetrol; Balsaminapentaol A
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
UNII
  • InChI=1S/C30H50O5/c1-17(2)25(35)22(32)14-18(3)19-10-11-30(7)26-23(33)15-21-20(8-9-24(34)28(21,5)16-31)27(26,4)12-13-29(19,30)6/h15,18-20,22-26,31-35H,1,8-14,16H2,2-7H3/t18-,19-,20-,22-,23+,24+,25-,26-,27+,28-,29-,30+/m1/s1 checkY
    Key: LJWAEAIXBCCHLR-ITWKNSBQSA-N checkY
  • C[C@H](C[C@@H](O)[C@H](O)C(C)=C)[C@@]1([H])CC[C@@]2(C)[C@]3([H])[C@@H](O)C=C4[C@@](C)(CO)[C@@H](O)CC[C@@]4([H])[C@]3(C)CC[C@@]21C
Properties
C30H50O5
Molar mass 490.725 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Balsaminepentaol is an amorphous powder soluble in methanol and ethyl acetate but insoluble in n-hexane. It is cytotoxic at about 50 μM.[1]

See also

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References

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  1. ^ a b Cátia Ramalhete; Tayyab A. Mansoor; Silva Mulhovo; Joseph Molnár & Maria-José U. Ferreira (2009). "Cucurbitane-Type Triterpenoids from the African Plant Momordica balsamina". Journal of Natural Products. 72 (11): 2009–2013. doi:10.1021/np900457u. hdl:10884/1322. PMID 19795842.