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Dammarane information


Dammarane
Names
IUPAC name
Dammarane[1]
Systematic IUPAC name
(1R,3aR,3bR,5aS,9aS,9bR,11aR)-1-[(2R)-6-Methylheptan-2-yl]-3a,3b,6,6,9a-pentamethylhexadecahydro-1H-cyclopenta[a]phenanthrene
Identifiers
CAS Number
  • 545-22-2
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:CHEBI:36488 ☒N
ChemSpider
  • 7827637 ☒N
KEGG
  • C22609
MeSH C102963
PubChem CID
  • 9548714
CompTox Dashboard (EPA)
  • DTXSID20969680 Edit this at Wikidata
InChI
  • InChI=1S/C30H54/c1-21(2)11-9-12-22(3)23-15-19-29(7)24(23)13-14-26-28(6)18-10-17-27(4,5)25(28)16-20-30(26,29)8/h21-26H,9-20H2,1-8H3/t22-,23-,24-,25+,26-,28+,29-,30-/m1/s1 ☒N
    Key: OORMXZNMRWBSTK-LGFJJATJSA-N ☒N
  • InChI=1/C30H54/c1-21(2)11-9-12-22(3)23-15-19-29(7)24(23)13-14-26-28(6)18-10-17-27(4,5)25(28)16-20-30(26,29)8/h21-26H,9-20H2,1-8H3/t22-,23-,24-,25+,26-,28+,29-,30-/m1/s1
    Key: OORMXZNMRWBSTK-LGFJJATJBV
SMILES
  • C[C@H](CCCC(C)C)[C@H]1CC[C@@]2([C@@H]1CC[C@H]3[C@]2(CC[C@@H]4[C@@]3(CCCC4(C)C)C)C)C
Properties
Chemical formula
C30H54
Molar mass 414.75 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Dammarane is a tetracyclic triterpene found in sapogenins (forming triterpenoid saponins) like those of ginseng (ginsenosides: panaxatriol and protopanaxadiol). Compounds of the series were first isolated from and named after dammar resin, a natural resin from the tropical trees of the Dipterocarp family.[2] [3]

  1. ^ International Union of Pure and Applied Chemistry (2014). Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013. The Royal Society of Chemistry. p. 1535. doi:10.1039/9781849733069. ISBN 978-0-85404-182-4.
  2. ^ Mills J.S.; Werner A.E.A. (1955). "The Chemistry of Dammar Resin". Journal of the Chemical Society: 3132–40. doi:10.1039/jr9550003132.
  3. ^ Mills J.S. (1956) "The Constitution of the Neutral, Tetracyclic Triterpenes of Dammar Resin" Journal of the Chemical Society 2196-2202

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Dammarane

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Dammarane is a tetracyclic triterpene found in sapogenins (forming triterpenoid saponins) like those of ginseng (ginsenosides: panaxatriol and protopanaxadiol)...

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Ginsenoside

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aglycones: the four-ring dammarane family, which contains the majority of known ginsenosides, and the oleanane family. The dammaranes further subdivided into...

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Bacoside

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chemical compounds isolated from Bacopa monnieri. Chemically, they are dammarane-type triterpenoid saponins. There are at least twelve known members of...

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Bacopa monnieri

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gastrointestinal upset. The best characterized phytochemicals in Bacopa monnieri are dammarane-type triterpenoid saponins known as bacosides, with jujubogenin or pseudo-jujubogenin...

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Panax notoginseng

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case is usually 1-3 g. P. notoginseng contains dammarane-type ginsenosides as major constituents. Dammarane-type ginsenosides includes 2 classifications:...

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Combretum rotundifolium

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Combretum found in South America. Combretum rotundifolium contains acidic dammarane arabinofuranosides. The bright yellow/red flowers are the decoration of...

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Dammar gum

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oxidation products. Many of them are low molecular weight compounds (dammarane, dammarenolic acid, oleanane, oleanonic acid, etc.), which easily oxidizes...

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Hodulcine

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Hodulcine (or hoduloside) are glycosides (dammarane-type triterpenes) which are isolated from the leaves of Hovenia dulcis Thunb. (Rhamnaceae) also known...

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Panaxatriol

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is an aglycone of ginsenosides, a group of steroid glycosides. It is a dammarane-type tetracyclic triterpene sapogenin found in ginseng (Panax ginseng)...

Word Count : 86

Gymnemic acid

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tongue can take more than 10 minutes. Other anti-sweeteners: Hodulcine, a dammarane-type triterpene glycoside from the leaves of Hovenia dulcis Lactisole...

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American ginseng

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American ginseng contains dammarane-type ginsenosides, or saponins, as the major biologically active constituents. Dammarane-type ginsenosides include...

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Euphane

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lanostane. Its derivatives are widely distributed in many plants. Protostane Dammarane Lanostane Calculated using Advanced Chemistry Development (ACD/Labs) Software...

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Protopanaxadiol

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is an aglycone of ginsenosides, a group of steroid glycosides. It is a dammarane-type tetracyclic terpene sapogenin found in ginseng (Panax ginseng) and...

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Protopanaxatriol

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is an aglycone of ginsenosides, a group of steroid glycosides. It is a dammarane-type tetracyclic triterpene sapogenins found in ginseng (Panax ginseng)...

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Protostane

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because it is considered to be the "prototype" of steroids. Fusidane Dammarane Lanostane International Union of Pure and Applied Chemistry (2014). Nomenclature...

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Fusidane

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a series of steroids, such as the antibiotic fusidic acid. Protostane Dammarane Cucurbitane Zhao M, Gödecke T, Gunn J, Duan JA, Che CT (2013). "Protostane...

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Lupeol

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polycyclization. Lupeol is produced by several organisms from squalene epoxide. Dammarane and baccharane skeletons are formed as intermediates. The reactions are...

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C30H54

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The molecular formula C30H54 may refer to: Baccharane Cucurbitane Dammarane Dinosterane Euphane 24-Isopropylcholestane Lanostane 24-n-Propylcholestane...

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Pseudoginsenoside F11

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ginsenoside Rf. The molecule is a triterpenoid saponin member of the dammarane family and contains a four-ring rigid skeleton. Compounds in the ginsenoside...

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Dammarene

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Dammarenes are derivatives of dammaranes that have a double bond. These compounds are often composed of saponins, examples include Protopanaxadiol and...

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