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Cucurbitane

Cucurbitane is a tetracyclic chemical compound with formula C30H54. It is a polycyclic hydrocarbon, specifically triterpene. It is also an isomer of lanostane, from which it differs by the formal shift of a methyl group from the 10 to the 9β position in the standard steroid numbering scheme.

Last revised
Jun 11, 2026
Read time
≈ 6 min
Length
1,472 w
Citations
82
Source
Wikipedia ↗
Cucurbitane
source ↗
Names
IUPAC name
19-Nor-5ξ,9β,10α-lanostane
Systematic IUPAC name
(1R,3aS,3bR,5aΞ,9aR,9bS,11aR)-3a,6,6,9b,11a-Pentamethyl-1-[(2R)-6-methylheptan-2-yl]hexadecahydro-1H-cyclopenta[a]phenanthrene
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
UNII
  • InChI=1S/C30H54/c1-21(2)11-9-12-22(3)23-16-18-30(8)26-15-14-24-25(13-10-17-27(24,4)5)28(26,6)19-20-29(23,30)7/h21-26H,9-20H2,1-8H3/t22-,23-,24-,25-,26-,28+,29-,30+/m1/s1 ☒N
    Key: ZYZJWAJOTPNVPI-AUAIAXQGSA-N ☒N
  • (5α): InChI=1/C30H54/c1-21(2)11-9-12-22(3)23-16-18-30(8)26-15-14-24-25(13-10-17-27(24,4)5)28(26,6)19-20-29(23,30)7/h21-26H,9-20H2,1-8H3/t22-,23-,24-,25-,26-,28+,29-,30+/m1/s1
    Key: ZYZJWAJOTPNVPI-AUAIAXQGBW
  • (5β): InChI=1/C30H54/c1-21(2)11-9-12-22(3)23-16-18-30(8)26-15-14-24-25(13-10-17-27(24,4)5)28(26,6)19-20-29(23,30)7/h21-26H,9-20H2,1-8H3/t22-,23-,24+,25-,26-,28+,29-,30+/m1/s1
    Key: ZYZJWAJOTPNVPI-QJMYWHNVBB
  • (5β): InChI=1S/C30H54/c1-21(2)11-9-12-22(3)23-16-18-30(8)26-15-14-24-25(13-10-17-27(24,4)5)28(26,6)19-20-29(23,30)7/h21-26H,9-20H2,1-8H3/t22-,23-,24+,25-,26-,28+,29-,30+/m1/s1
    Key: ZYZJWAJOTPNVPI-QJMYWHNVSA-N
  • (5α): C[C@H](CCCC(C)C)[C@@]1([H])CC[C@@]2(C)[C@]3([H])CC[C@@]4([H])C(C)(C)CCC[C@@]4([H])[C@]3(C)CC[C@@]21C
  • (5β): C[C@H](CCCC(C)C)[C@@]1([H])CC[C@@]2(C)[C@]3([H])CC[C@]4([H])C(C)(C)CCC[C@@]4([H])[C@]3(C)CC[C@@]21C
Properties
C30H54
Molar mass 414.762 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

Cucurbitane is a tetracyclic chemical compound with formula C
30H
54. It is a polycyclic hydrocarbon, specifically triterpene. It is also an isomer of lanostane (specifically 19(10→9β)-abeolanostane), from which it differs by the formal shift of a methyl group (carbon number 19) from the 10 to the 9β position in the standard steroid numbering scheme.12

The name is applied to two stereoisomers, distinguished by the prefixes 5α- and 5β-, which differ by the handedness of the bonds at a particular carbon atom (number 5 in the standard steroid numbering scheme).1

  • 5α-Cucurbitane
    5α-Cucurbitane
  • 5β-Cucurbitane
    5β-Cucurbitane

Cucurbitane is the core chemical structure of a class of derivatives known as cucurbitane-type triterpenoids or simply as cucurbitanes.3

Derivatives

Natural compounds

Compounds with the basic cucurbitane skeleton are found in many plants, and some are important phytopharmaceuticals.4 Natural cucurbitane-related compounds include:

Named

Unnamed

  • 3β,7β,23ξ-trihydroxycucurbita-5,24-dien-19-al, soluble in chloroform, melts at 123−125 °C, from Momordica charantia, Momordica foetida.24: 1 
  • 3β,7β,25-trihydroxycucurbita-5,23-dien-19-al, soluble in chloroform, melts at 188−191 °C, from Momordica charantia, Momordica foetida24: 2 
  • 3β,7β-dihydroxy-25-methoxycucurbita-5,23-dien-19-al, soluble in chloroform, from Momordica charantia, Momordica foetida24: 3 
  • 5β,19-epoxy-25-methoxycucurbita-6,23-dien-3β,19-diol, soluble in chloroform, melts at 182−184 °C, from Momordica foetida24: 4 
  • 5β,19-epoxycucurbita-6,23-dien-3β,19,25-triol, soluble in chloroform, from Momordica foetida24: 5 
  • 5β,19-epoxy-19-methoxycucurbita-6,23-dien-3β,25-diol, soluble in chloroform, melts at 102−104 °C, from Momordica charantia, Momordica foetida24: 6 
  • 5β,19-epoxy-19,25-dimethoxycucurbita-6,23-dien-3β-ol, soluble in chloroform, from Momordica charantia, Momordica foetida24: 7 
  • 5β,19-epoxy-25-methoxycucurbita-6,23-dien-3β-ol, soluble in chloroform, melts at 139−141 °C, from Momordica charantia, Momordica foetida24: 8 
  • 19(R)-n-butanoxy-5β,19-epoxycucurbita-6,23-diene-3β,25-diol 3-O-β-glucopyranoside, C
    40    H
    66    O
    9    , white powder soluble in methanol, from Momordica charantia fruit (8 mg/35 kg)19: 1 
  • 23-O-β-allopyranosylecucurbita-5,24-dien-7α,3β,22(R),23(S)-tetraol 3-O-β-allopyranoside,C
    42    H
    69    O
    14    , white powder soluble in methanol, from Momordica charantia fruit (10 mg/35 kg)19: 2 
  • 23(R),24(S),25-trihydroxycucurbit-5-ene 3-O-{[β-glucopyranosyl(1→6)]-O-β-glucopyranosyl}-25-O-β-glucopyranoside, C
    48    H
    82    O
    19    , white powder soluble in methanol, from Momordica charantia fruit (10 mg/35 kg)19: 3 
  • 2,16-dihydroxy-22,23,24,25,26,27-hexanorcucurbit-5-en-11,20-dione 2-O-β-D-glucopyranoside, soluble in ethanol, from Cucurbita pepo fruits (25 mg/15 kg)9: 3 
  • 16-hydroxy-22,23,24,25,26,27-hexanorcucurbit-5-en-11,20-dione 3-O-α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranoside, white powder, soluble in ethanol, from Cucurbita pepo fruits (12 mg/15 kg)9: 4 
  • 7-methoxycucurbita-5,24-diene-3β,23(R)-diol, from Momordica balsamina25
  • 25,26,27-trinorcucurbit-5-ene-3,7,23-trione C
    27    H
    40    O
    3    , white powder, soluble in methanol, from stems of Momordica charantia (6 mg/18 kg)23: 3 
See also

See also

  • Goyaglicoside
  • Karaviloside
  • Momordenol, from Momordica charantia16
  • 24(R)-stigmastan-3β,5α,6β-triol-25-ene 3-O-β-glucopyranoside, C
    35    H
    60    O
    8    , white powder, from Momordica charantia fruit (15 mg/35 kg)19: 4 
References

References

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  2. Satish Kumar and Raj Kumar (1991), Dictionary of Biochemistry. Anmol Publications, India
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