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Gonane

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Gonane
Stereo, skeletal formula of gonane ((1R,2S,10S,11R,15S)-heptadecane) with all chiral centres hydrogenised
Carbon numbering in gonane
Names
IUPAC name
2(8S,9R,10S,13S,14R)-2,3,4,5,6,7,8,9,10,11,12,13,14,15,16,17-hexadecahydro-1H-cyclopenta[a]phenanthrene
Identifiers
  • 4732-76-7 (1R,2S,10S,11R,15S)- heptadecane ☒N
3D model (JSmol)
ChEBI
ChemSpider
  • 5256859 (1R,2S,10S,11R,15S)- heptadecane checkY
  • 5256861 (1R,2S,7R,10S,11R,15S)- heptadecane checkY
  • 5256860 (1R,2S,7S,10S,11R,15S)- heptadecane checkY
  • 1077 checkY
KEGG
  • 1108
  • 6857523 (1R,2S,10S,11R,15S)- heptadecane
  • 6857525 (1R,2S,7R,10S,11R,15S)- heptadecane
  • 6857524 (1R,2S,7S,10S,11R,15S)- heptadecane
  • InChI=1S/C17H28/c1-2-6-14-12(4-1)8-10-17-15-7-3-5-13(15)9-11-16(14)17/h12-17H,1-11H2/t12?,13-,14-,15+,16+,17-/m0/s1 checkY
    Key: UACIBCPNAKBWHX-CTBOZYAPSA-N checkY
  • C2C1[C@H](CCCC1)[C@H]3CC[C@H]4[C@H]([C@@H]3C2)CCC4
Properties
C17H28
Molar mass 232.411 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 ?)

Gonane (C17), also known as perhydrocyclopenta[a]phenanthrene, is a tetracyclic hydrocarbon ring structure and the fundamental steroid nucleus.[1][2] It consists of a phenanthrene ring fused with a cyclopentane ring. Unlike steroid hormones, gonane has no methyl groups at the C10 and C13 positions and no side chain at the C17 position.[2] Because gonane has six centers of chirality, it has 64 (26) theoretically possible stereoisomers.[1] However, only a few of these stereoisomers are actually encountered with steroids.[1] The most common stereoisomers of gonane are 5α-gonane and 5β-gonane.

  • 5α-Gonane
    5α-Gonane
  • 5β-Gonane
    5β-Gonane
  • 5α-Gonane, side-perspective view
    5α-Gonane, side-perspective view
  • 5β-Gonane, side-perspective view
    5β-Gonane, side-perspective view

Estrane (C18) is the 13β-methyl variant of gonane, androstane (C19) is the 10β,13β-dimethyl variant of gonane, and pregnane (C21) is the 10β,13β-dimethyl, 17β-ethyl variant of gonane.[3][4]

References

  1. ^ a b c Burkhard Fugmann; Susanne Lang-Fugmann; Wolfgang Steglich (28 May 2014). RÖMPP Encyclopedia Natural Products, 1st Edition, 2000. Thieme. pp. 1918–. ISBN 978-3-13-179551-9.
  2. ^ a b James G. Speight (24 December 2010). Handbook of Industrial Hydrocarbon Processes. Gulf Professional Publishing. pp. 474–. ISBN 978-0-08-094271-1.
  3. ^ D. Sriram (1 September 2010). Medicinal Chemistry. Pearson Education India. pp. 594–. ISBN 978-81-317-3144-4.
  4. ^ Etienne-Emile Baulieu; Paul A. Kelly (30 November 1990). Hormones: From Molecules to Disease. Springer Science & Business Media. pp. 391–. ISBN 978-0-412-02791-8.


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