Lanostane: Difference between revisions

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	{{Chembox		{{Chembox
			\| Verifiedfields = changed
⚫	\| verifiedrevid = ~~406403199~~
			\| Watchedfields = changed
		⚫	\| verifiedrevid = 424957756
	\| ImageFile = Lanostane.svg		\| ImageFile = Lanostane.svg
	\| ~~ImageSize~~ = ~~200px~~		\| ImageAlt =
	\| ~~ImageAlt~~ =		\| ImageSize = 250
	\| IUPACName =		\| IUPACName =
	\| OtherNames = 4,4,14-Trimethylcholestane		\| OtherNames = 4,4,14α-Trimethylcholestane
	\| Section1 = {{Chembox Identifiers		\|Section1={{Chembox Identifiers
	\| CASNo = 474-20-4		\| CASNo = 474-20-4
	\| CASNo_Comment = (5α)		\| CASNo_Comment = (5α)
	\| CASNo_Ref = {{cascite\|correct\|CAS}}		\| CASNo_Ref = {{cascite\|correct\|CAS}}
	\| CASNo1 = 57496-02-3		\| CASNo1 = 57496-02-3
	\| CASNo1_Comment = (5β)		\| CASNo1_Comment = (5β)
	\| CASNo1_Ref = {{cascite\|correct\|CAS}}		\| CASNo1_Ref = {{cascite\|correct\|CAS}}
	\| ~~PubChem~~ =		\| PubChem1 = 9548665
			\| PubChem1_Comment = (5α)
⚫	\| SMILES1 = C(CCCC(C)C)1()CC2(C)3()CC4()C(C)(C)CCC4(C)3()CC21C
			\| ChemSpiderID_Ref = {{chemspidercite\|changed\|chemspider}}
⚫	\| SMILES1_Comment = (5α)
			\| ChemSpiderID = 7827588
⚫	\| SMILES2 = C(CCCC(C)C)1()CC2(C)3()CC4()C(C)(C)CCC4(C)3()CC21C
	\| ~~SMILES2_Comment~~ = (5β)		\| ChemSpiderID_Comment = (5α)
			\| ChEBI_Ref = {{ebicite\|changed\|EBI}}
			\| ChEBI = 20265
			\| ChEBI_Comment = (5α)
		⚫	\| SMILES1 = C(CCCC(C)C)1()CC2(C)3()CC4()C(C)(C)CCC4(C)3()CC21C
		⚫	\| SMILES1_Comment = (5α)
		⚫	\| SMILES2 = C(CCCC(C)C)1()CC2(C)3()CC4()C(C)(C)CCC4(C)3()CC21C
			\| SMILES2_Comment = (5β)
			\| InChI = 1/C30H54/c1-21(2)11-9-12-22(3)23-15-19-30(8)25-13-14-26-27(4,5)17-10-18-28(26,6)24(25)16-20-29(23,30)7/h21-26H,9-20H2,1-8H3/t22-,23-,24+,25-,26+,28-,29-,30+/m1/s1
			\| InChI_Comment = (5α)
			\| InChIKey = ZQIOPEXWVBIZAV-ZKYCIREVBA
			\| StdInChI_Ref = {{stdinchicite\|changed\|chemspider}}
			\| StdInChI = 1S/C30H54/c1-21(2)11-9-12-22(3)23-15-19-30(8)25-13-14-26-27(4,5)17-10-18-28(26,6)24(25)16-20-29(23,30)7/h21-26H,9-20H2,1-8H3/t22-,23-,24+,25-,26+,28-,29-,30+/m1/s1
			\| StdInChI_Comment = (5α)
			\| StdInChIKey_Ref = {{stdinchicite\|changed\|chemspider}}
			\| StdInChIKey = ZQIOPEXWVBIZAV-ZKYCIREVSA-N
			}}
		⚫	\|Section2={{Chembox Properties
		⚫	\| C=30 \| H=54
		⚫	\| Appearance =
		⚫	\| Density =
			\| MeltingPtC = 98 to 99
		⚫	\| MeltingPt_ref = <ref>{{cite journal \| doi = 10.1002/hlca.19500330658 \| author = Voser, W. \| last2 = Montavon \| first2 = M. \| last3 = Günthard \| first3 = Hs. H. \| last4 = Jeger \| first4 = O. \| last5 = Ruzicka \| first5 = L. \| title = Zur Kenntnis der Triterpene. 156. Mitteilung. Zur Konstitution des Lanostadienols \| journal = Helvetica Chimica Acta \| year = 1950 \| volume = 33 \| issue = 6 \| pages = 1893–1910}}</ref>
		⚫	\| BoilingPt =
		⚫	\| Solubility =
			}}
		⚫	\|Section3={{Chembox Hazards
		⚫	\| MainHazards =
		⚫	\| FlashPt =
			\| AutoignitionPt =
	}}		}}
⚫	\| Section2 = {{Chembox Properties
⚫	\| C=30 \| H=54
⚫	\| Appearance =
⚫	\| Density =
⚫	\| ~~MeltingPt~~ = ~~98-99 °C~~<ref>{{cite journal \| doi = 10.1002/hlca.19500330658 \| author = Voser, W. \| last2 = Montavon \| first2 = M. \| last3 = Günthard \| first3 = Hs. H. \| last4 = Jeger \| first4 = O. \| last5 = Ruzicka \| first5 = L. \| title = Zur Kenntnis der Triterpene. 156. Mitteilung. Zur Konstitution des Lanostadienols \| journal = Helvetica Chimica Acta \| year = 1950 \| volume = 33 \| pages = 1893–1910}}</ref>
⚫	\| BoilingPt =
⚫	\| Solubility = }}
⚫	\| Section3 = {{Chembox Hazards
⚫	\| MainHazards =
⚫	\| FlashPt =
	\| Autoignition = }}
	}}		}}

	'''Lanostane''' or '''4,4,14-trimethylcholestane''' is a ] with formula {{chem\|C\|30\|H\|54}}. It is a ], specifically a ]. It is an isomer of ].		'''Lanostane''' or '''4,4,14α-trimethylcholestane''' is a ] ] with formula {{chem\|C\|30\|H\|54}}. It is a ], specifically a ]. It is an isomer of ].

	The name is applied to two ]s, distinguished by the prefixes '''5α-''' and '''5β-''', which differ by the handedness of the bonds at a particular ] atom (number 5 in the standard steroid numbering scheme).<ref name=iupac69/>		The name is applied to two ]s, distinguished by the prefixes '''5α-''' and '''5β-''', which differ by the handedness of the bonds at a particular ] atom (number 5 in the standard steroid numbering scheme).<ref name=iupac69/>
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	</gallery>		</gallery>

	Replacement of a ] atom attached to ] number 3 in the 5α isomer with a ] results in ], the ] ] of the ]s in animals.<ref name=iupac69>IUPAC Commission on the Nomenclature of Organic Chemistry and IUPAC-IUB Commission on Biochemical Nomenclature (1969), ''The Nomenclature of Steroids - Revised Tentative Rules~~''.~~ European J. of Biochemistry, volume 10, 1-19</ref>		Replacement of a ] atom attached to ] number 3 in the 5α isomer with a ] results in ], the ] ] of the ]s in animals.<ref name=iupac69>{{cite journal \|author=IUPAC Commission on the Nomenclature of Organic Chemistry and IUPAC-IUB Commission on Biochemical Nomenclature \|year=1969 \|title=The Nomenclature of Steroids — Revised Tentative Rules \|journal=European Journal of Biochemistry \|volume=10 \|issue=1 \|pages=1–19 \|doi=10.1111/j.1432-1033.1969.tb00650.x \|doi-access=free }}</ref>

	==References==		==References==
	{{reflist}}		{{reflist}}

			{{Saponins}}
⚫	]
			{{Tetracyclics}}

		⚫	]
	]		]

Latest revision as of 23:07, 8 December 2023

Lanostane
Names

Other names 4,4,14α-Trimethylcholestane
Identifiers
CAS Number	474-20-4 (5α) 57496-02-3 (5β)
3D model (JSmol)	(5α): Interactive image (5β): Interactive image
ChEBI	CHEBI:20265 (5α)
ChemSpider	7827588 (5α)
PubChem CID	9548665 (5α)
CompTox Dashboard (EPA)	DTXSID60963824
InChI InChI=1S/C30H54/c1-21(2)11-9-12-22(3)23-15-19-30(8)25-13-14-26-27(4,5)17-10-18-28(26,6)24(25)16-20-29(23,30)7/h21-26H,9-20H2,1-8H3/t22-,23-,24+,25-,26+,28-,29-,30+/m1/s1Key: ZQIOPEXWVBIZAV-ZKYCIREVSA-N (5α): InChI=1/C30H54/c1-21(2)11-9-12-22(3)23-15-19-30(8)25-13-14-26-27(4,5)17-10-18-28(26,6)24(25)16-20-29(23,30)7/h21-26H,9-20H2,1-8H3/t22-,23-,24+,25-,26+,28-,29-,30+/m1/s1Key: ZQIOPEXWVBIZAV-ZKYCIREVBA
SMILES (5α): C(CCCC(C)C)1()CC2(C)3()CC4()C(C)(C)CCC4(C)3()CC21C (5β): C(CCCC(C)C)1()CC2(C)3()CC4()C(C)(C)CCC4(C)3()CC21C
Properties
Chemical formula	C₃₀H₅₄
Molar mass	414.762 g·mol
Melting point	98 to 99 °C (208 to 210 °F; 371 to 372 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). N verify (what is ?) Infobox references

Chemical compound

Lanostane or 4,4,14α-trimethylcholestane is a tetracyclic chemical compound with formula C
₃₀H
₅₄. It is a polycyclic hydrocarbon, specifically a triterpene. It is an isomer of cucurbitane.

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).

5α-Lanostane
5β-Lanostane

Replacement of a hydrogen atom attached to carbon number 3 in the 5α isomer with a hydroxyl group results in lanosterol, the biogenetic precursor of the steroids in animals.

References

Voser, W.; Montavon, M.; Günthard, Hs. H.; Jeger, O.; Ruzicka, L. (1950). "Zur Kenntnis der Triterpene. 156. Mitteilung. Zur Konstitution des Lanostadienols". Helvetica Chimica Acta. 33 (6): 1893–1910. doi:10.1002/hlca.19500330658.
^ IUPAC Commission on the Nomenclature of Organic Chemistry and IUPAC-IUB Commission on Biochemical Nomenclature (1969). "The Nomenclature of Steroids — Revised Tentative Rules". European Journal of Biochemistry. 10 (1): 1–19. doi:10.1111/j.1432-1033.1969.tb00650.x.

Saponin Glycosides

Sapogenin (aglycone)

Steroidal
(C₂₇ skeleton)

Triterpene
(C₃₀ skeleton)

Tetracyclic	Lanostane Dammarane
Pentacyclic	Lupane Oleanane Hederagenin Enoxolone Maslinic acid Ursane Hopane

Glycone

v t e Tetracyclics
Classes	Polyketides Tetracenes Steroids
Antibiotics	Tetracyclines Tetracycline Chlortetracycline Demeclocycline Doxycycline Eravacycline Lymecycline Minocycline Omadacycline Oxytetracycline Rolitetracycline Sarecycline Glycylcyclines Tigecycline Triterpenes Fusidanes Fusidic acid Helvolic acid Cephalosporin P₁
Antidepressants (TeCAs)	Azipramine Ciclopramine Esmirtazapine Mianserin Mirtazapine Naranol Oxaprotiline Setiptiline
Steroids	Gonanes Steranes Cholane Cholestane Ergostane Sex hormone steroids Androstanes Androstenediol Dehydroepiandrosterone Testosterone Estranes Estetrol Estradiol Estriol Estrone Pregnanes Progestogens Progesterone Progestins Acetomepregenol Chlormadinone acetate Danazol Delmadinone acetate Etonogestrel Gestodene Hydroxyprogesterone caproate Levonorgestrel Norethisterone Norgestrel Segesterone acetate Tibolone Corticosteroids Cortisone Cortisol Prednisone Prednisolone Aldosterone Allopregnanes Norpregnane Retropregnane Sterols Phytosterols Campesterol beta-Sitosterol Ergosterols Secosteroids Ergocalciferol Cholecalciferol Cholesterol Stanol esters Triterpenes Cycloartane Cucurbitacins Cucurbitane Dammarane Euphane Lanostane Protostane

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