Steroid (English Wikipedia)

Analysis of information sources in references of the Wikipedia article "Steroid" in English language version.

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"R-2.4.1 Fusion nomenclature". Archived from the original on 22 November 2023. Retrieved 22 November 2023.

acs.org

"Russell Marker Creation of the Mexican Steroid Hormone Industry". International Historic Chemical Landmark. American Chemical Society. Archived from the original on 12 February 2020. Retrieved 10 May 2014.

arkat-usa.org

Wolfing J (2007). "Recent developments in the isolation and synthesis of D-homosteroids and related compounds". Arkivoc. 2007 (5): 210–230. doi:10.3998/ark.5550190.0008.517. hdl:2027/spo.5550190.0008.517. Archived from the original on 1 February 2013. Retrieved 20 May 2014.

auho.com

books.auho.com

Rogozkin VA (14 June 1991). "Anabolic Androgenic Steroids: Structure, Nomenclature, and Classification, Biological Properties". Metabolism of Anabolic-Androgenic Steroids. CRC Press. pp. 1–. ISBN 978-0-8493-6415-0. The steroid structural base is a steran nucleus, a polycyclic C17 steran skeleton consisting of three condensed cyclohexane rings in nonlinear or phenanthrene junction (A, B, and C), and a cyclopentane ring (D).1,2^{[permanent dead link]}

books.google.com

Arago F, Gay-Lussac JL (1816). Annales de chimie et de physique (Annals of Chemistry and Physics) (in French). Chez Crochard. p. 346. "Je nommerai cholesterine, de χολη, bile, et στερεος, solide, la substance cristallisée des calculs biliares humains, ... " (I will name cholesterine – from χολη (bile) and στερεος (solid) – the crystalized substance from human gallstones ... )
Also available in print at Hill RA, Makin HL, Kirk DN, Murphy GM (1991). Dictionary of Steroids. London, GBR: Chapman and Hall. pp. xxx–lix. ISBN 978-0-412-27060-4. Retrieved 20 June 2015.
Urich K (16 September 1994). "Sterols and Steroids". Comparative Animal Biochemistry. Springer Science & Business Media. pp. 624–. ISBN 978-3-540-57420-0.
Greep 2013. Greep RO, ed. (22 October 2013). "Cortoic acids". Recent Progress in Hormone Research: Proceedings of the 1979 Laurentian Hormone Conference. Elsevier Science. pp. 345–391. ISBN 978-1-4832-1956-1.
Gao G, Chen C (2012). "Nakiterpiosin". In Corey EJ, Li JJ (eds.). Total synthesis of natural products: at the frontiers of organic chemistry. Berlin: Springer. doi:10.1007/978-3-642-34065-9. ISBN 978-3-642-34064-2. S2CID 92690863.

britannica.com

Biological significance of steroids. Archived from the original on 12 February 2024. Retrieved 12 February 2024.
androgen. 19 January 2024. Archived from the original on 29 January 2024. Retrieved 12 February 2024.

creativecommons.org

Masiutin MM, Yadav MK (3 April 2023). "Alternative androgen pathways" (PDF). WikiJournal of Medicine. 10: 29. doi:10.15347/WJM/2023.003. S2CID 257943362. This article incorporates text from this source, which is available under the CC BY 4.0 license.

deutsche-digitale-bibliothek.de

Chevreul ME (8 May 1815). "Recherches chimiques sur les corps gras, et particulièrement sur leurs combinaisons avec les alcalis. Sixième mémoire. Examen des graisses d'homme, de mouton, de boeuf, de jaguar et d'oie" [Chemical research on fatty substances, and particularly on their combinations with alkalis. Sixth memoir. Examination of human, sheep, beef, jaguar and goose fats]. Annales de Chimie et de Physique (Annals of Chemistry and Physics) (in French). 2: 339–372. Archived from the original on 4 October 2023. Retrieved 11 September 2023 – via Deutsche Digitale Bibliothek.

doi.org

Moss GP, the Working Party of the IUPAC-IUB Joint Commission on Biochemical Nomenclature (1989). "Nomenclature of steroids, recommendations 1989" (PDF). Pure Appl. Chem. 61 (10): 1783–1822. doi:10.1351/pac198961101783. S2CID 97612891. Archived (PDF) from the original on 30 November 2012. Retrieved 21 February 2012. Also available with the same authors at "IUPAC-IUB Joint Commission on Biochemical Nomenclature (JCBN). The nomenclature of steroids. Recommendations 1989". European Journal of Biochemistry. 186 (3): 429–458. December 1989. doi:10.1111/j.1432-1033.1989.tb15228.x. PMID 2606099.; Also available online at "The Nomenclature of Steroids". London, GBR: Queen Mary University of London. p. 3S-1.4. Archived from the original on 10 September 2017. Retrieved 10 May 2014.
Rhen T, Cidlowski JA (October 2005). "Antiinflammatory action of glucocorticoids--new mechanisms for old drugs". The New England Journal of Medicine. 353 (16): 1711–1723. doi:10.1056/NEJMra050541. PMID 16236742. S2CID 5744727.
Yang Y, Krin A, Cai X, Poopari MR, Zhang Y, Cheeseman JR, Xu Y (January 2023). "Conformations of Steroid Hormones: Infrared and Vibrational Circular Dichroism Spectroscopy". Molecules. 28 (2): 771. doi:10.3390/molecules28020771. PMC 9864676. PMID 36677830.
Masiutin MM, Yadav MK (3 April 2023). "Alternative androgen pathways" (PDF). WikiJournal of Medicine. 10: 29. doi:10.15347/WJM/2023.003. S2CID 257943362. This article incorporates text from this source, which is available under the CC BY 4.0 license.
"IUPAC-IUB Joint Commission on Biochemical Nomenclature (JCBN). The nomenclature of steroids. Recommendations 1989". Eur J Biochem. 186 (3): 430. 1989. doi:10.1111/j.1432-1033.1989.tb15228.x. PMID 2606099. p. 430: 3S‐1.0. Definition of steroids and sterols. Steroids are compounds possessing the skeleton of cyclopenta[a]phenanthrene or a skeleton derived therefrom by one or more bond scissions or ring expansions or contractions. Methyl groups are normally present at C-10 and C-13. An alkyl side chain may also be present at C-17. Sterols are steroids carrying a hydroxyl group at C-3 and most of the skeleton of cholestane.
"IUPAC-IUB Joint Commission on Biochemical Nomenclature (JCBN). The nomenclature of steroids. Recommendations 1989". Eur J Biochem. 186 (3): 429–458. 1989. doi:10.1111/j.1432-1033.1989.tb15228.x. PMID 2606099. p. 441: 3S-4. FUNCTIONAL GROUPS. 3S-4.0. General. Nearly all biologically important steroids are derivatives of the parent hydrocarbons (cf. Table 1) carrying various functional groups. [...] Suffixes are added to the name of the saturated or unsaturated parent system (see 33-2.5), the terminal e of -ane, -ene, -yne, -adiene etc. being elided before a vowel (presence or absence of numerals has no effect on such elisions).
"IUPAC-IUB Joint Commission on Biochemical Nomenclature (JCBN). The nomenclature of steroids. Recommendations 1989, chapter 3S-4.9". European Journal of Biochemistry. 186 (3): 429–458. December 1989. doi:10.1111/j.1432-1033.1989.tb15228.x. PMID 2606099. Archived from the original on 19 February 2024. Retrieved 19 February 2024. 3S‐4.9. Trivial names of important steroids Examples of trivial names retained for important steroid derivatives, these being mostly natural compounds of significant biological activity, are given in Table 2
"IUPAC-IUB Joint Commission on Biochemical Nomenclature (JCBN). The nomenclature of steroids. Recommendations 1989, chapter 3S-1.4". European Journal of Biochemistry. 186 (3): 429–458. December 1989. doi:10.1111/j.1432-1033.1989.tb15228.x. PMID 2606099. p. 431: 3S‐1.4. Orientation of projection formulae. When the rings of a steroid are denoted as projections onto the plane of the paper, the formula is normally to be oriented as in 2a. An atom or group attached to a ring depicted as in the orientation 2a is termed α (alpha) if it lies below the plane of the paper or β (beta) if it lies above the plane of the paper.
Favre HA, Powell WH (2014). "P-91". Nomenclature of Organic Chemistry – IUPAC Recommendations and Preferred Names 2013. The Royal Society of Chemistry. doi:10.1039/9781849733069. ISBN 978-0-85404-182-4. p. 868: P‐91.2.1.1 Cahn-Ingold-Prelog (CIP) stereodescriptors. Some stereodescriptors described in the Cahn-Ingold-Prelog (CIP) priority system, called 'CIP stereodescriptors', are recommended to specify the configuration of organic compounds, as described and exemplified in this Chapter and applied in Chapters P‐1 through P‐8, and in the nomenclature of natural products in Chapter P-10. The following stereodescriptors are used as preferred stereodescriptors (see P‐92.1.2): (a) 'R' and 'S', to designate the absolute configuration of tetracoordinate (quadriligant) chirality centers;
Favre HA, Powell WH (2014). "P-13.8.1.1". Nomenclature of Organic Chemistry – IUPAC Recommendations and Preferred Names 2013. The Royal Society of Chemistry. doi:10.1039/9781849733069. ISBN 978-0-85404-182-4. p. 66: P‐13.8.1.1 The prefix 'de' (not 'des'), followed by the name of a group or atom (other than hydrogen), denotes removal (or loss) of that group and addition of the necessary hydrogen atoms, i.e., exchange of that group with hydrogen atoms. As an exception, 'deoxy', when applied to hydroxy compounds, denotes the removal of an oxygen atom from an –OH group with the reconnection of the hydrogen atom. 'Deoxy' is extensively used as a subtractive prefix in carbohydrate nomenclature (see P‐102.5.3).
"IUPAC-IUB Joint Commission on Biochemical Nomenclature (JCBN). The nomenclature of steroids. Recommendations 1989". Eur J Biochem. 186 (3): 430. 1989. doi:10.1111/j.1432-1033.1989.tb15228.x. PMID 2606099. p. 430: 3S-1.1. Numbering and ring letters. Steroids are numbered and rings are lettered as in formula 1
"IUPAC-IUB Joint Commission on Biochemical Nomenclature (JCBN). The nomenclature of steroids. Recommendations 1989". Eur J Biochem. 186 (3): 436–437. 1989. doi:10.1111/j.1432-1033.1989.tb15228.x. PMID 2606099. p. 436-437: 3S‐2.5 Unsaturation. Unsaturation is indicated by changing -ane to -ene, -adiene, -yne etc., or -an- to -en-, -adien-, -yn- etc. Examples: Androst-5-ene, not 5-androstene; 5α-Cholest-6-ene; 5β-Cholesta-7,9(11)-diene; 5α-Cholest-6-en-3β-ol. Notes. 1) It is now recommended that the locant of a double bond is always adjacent to the syllable designating the unsaturation.[...] 3) The use of Δ (Greek capital delta) character is not recommended to designate unsaturation in individual names. It may be used, however, in generic terms, like 'Δ⁵-steroids'
Favre HA, Powell WH (2014). "P-3". Nomenclature of Organic Chemistry – IUPAC Recommendations and Preferred Names 2013. The Royal Society of Chemistry. doi:10.1039/9781849733069. ISBN 978-0-85404-182-4. P-31.2.2 General methodology. 'Hydro' and 'dehydro' prefixes are associated with hydrogenation and dehydrogenation, respectively, of a double bond; thus, multiplying prefixes of even values, as 'di', 'tetra', etc. are used to indicate the saturation of double bond(s), for example 'dihydro', 'tetrahydro'; or creation of double (or triple) bonds, as 'didehydro', etc. In names, they are placed immediately at the front of the name of the parent hydride and in front of any nondetachable prefixes. Indicated hydrogen atoms have priority over 'hydro' prefixes for low locants. If indicated hydrogen atoms are present in a name, the 'hydro' prefixes precede them.
Miller WL, Auchus RJ (February 2011). "The molecular biology, biochemistry, and physiology of human steroidogenesis and its disorders". Endocr Rev. 32 (1): 81–151. doi:10.1210/er.2010-0013. PMC 3365799. PMID 21051590.
Makin HL, Trafford DJ (1972). "The chemistry of the steroids". Clinics in Endocrinology and Metabolism. 1 (2): 333–360. doi:10.1016/S0300-595X(72)80024-0.
Bongiovanni AM, Clayton GW (March 1954). "Simplified method for estimation of 11-oxygenated neutral 17-ketosteroids in urine of individuals with adrenocortical hyperplasia". Proceedings of the Society for Experimental Biology and Medicine. 85 (3): 428–429. doi:10.3181/00379727-85-20905. PMID 13167092. S2CID 8408420.
Slaunwhite Jr WR, Neely L, Sandberg AA (1964). "The metabolism of 11-Oxyandrogens in human subjects". Steroids. 3 (4): 391–416. doi:10.1016/0039-128X(64)90003-0.
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Favre H, Powell W (2014). "Appendix 2". Nomenclature of Organic Chemistry – IUPAC Recommendations and Preferred Names 2013. The Royal Society of Chemistry. doi:10.1039/9781849733069. ISBN 978-0-85404-182-4. p. 1112: oxy* –O– P-15.3.1.2.1.1; P-63.2.2.1.1
Barrientos EJ, Lapuerta M, Boehman AL (August 2013). "Group additivity in soot formation for the example of C-5 oxygenated hydrocarbon fuels". Combustion and Flame. 160 (8): 1484–1498. Bibcode:2013CoFl..160.1484B. doi:10.1016/j.combustflame.2013.02.024.
"IUPAC-IUB Joint Commission on Biochemical Nomenclature (JCBN). The nomenclature of steroids. Recommendations 1989". Eur J Biochem. 186 (3): 429–58. 1989. doi:10.1111/j.1432-1033.1989.tb15228.x. PMID 2606099. p. 430: The prefix oxo- should also be used in connection with generic terms, e.g., 17-oxo steroids. The term '17-keto steroids', often used in the medical literature, is incorrect because C-17 is specified twice, as the term keto denotes C=O
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Siedenburg G, Jendrossek D (June 2011). "Squalene-hopene cyclases". Applied and Environmental Microbiology. 77 (12): 3905–15. Bibcode:2011ApEnM..77.3905S. doi:10.1128/AEM.00300-11. PMC 3131620. PMID 21531832.
Wink M (September 2003). "Evolution of secondary metabolites from an ecological and molecular phylogenetic perspective". Phytochemistry. 64 (1): 3–19. Bibcode:2003PChem..64....3W. doi:10.1016/S0031-9422(03)00300-5. PMID 12946402.
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Wolfing J (2007). "Recent developments in the isolation and synthesis of D-homosteroids and related compounds". Arkivoc. 2007 (5): 210–230. doi:10.3998/ark.5550190.0008.517. hdl:2027/spo.5550190.0008.517. Archived from the original on 1 February 2013. Retrieved 20 May 2014.
Gao G, Chen C (2012). "Nakiterpiosin". In Corey EJ, Li JJ (eds.). Total synthesis of natural products: at the frontiers of organic chemistry. Berlin: Springer. doi:10.1007/978-3-642-34065-9. ISBN 978-3-642-34064-2. S2CID 92690863.
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etymonline.com

Harper D. "sterol | Etymology, origin and meaning of sterol by etymonline". Online Etymology Dictionary. Archived from the original on 19 March 2023. Retrieved 19 March 2023.

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handle.net

hdl.handle.net

Wolfing J (2007). "Recent developments in the isolation and synthesis of D-homosteroids and related compounds". Arkivoc. 2007 (5): 210–230. doi:10.3998/ark.5550190.0008.517. hdl:2027/spo.5550190.0008.517. Archived from the original on 1 February 2013. Retrieved 20 May 2014.

harvard.edu

ui.adsabs.harvard.edu

Barrientos EJ, Lapuerta M, Boehman AL (August 2013). "Group additivity in soot formation for the example of C-5 oxygenated hydrocarbon fuels". Combustion and Flame. 160 (8): 1484–1498. Bibcode:2013CoFl..160.1484B. doi:10.1016/j.combustflame.2013.02.024.
Siedenburg G, Jendrossek D (June 2011). "Squalene-hopene cyclases". Applied and Environmental Microbiology. 77 (12): 3905–15. Bibcode:2011ApEnM..77.3905S. doi:10.1128/AEM.00300-11. PMC 3131620. PMID 21531832.
Wink M (September 2003). "Evolution of secondary metabolites from an ecological and molecular phylogenetic perspective". Phytochemistry. 64 (1): 3–19. Bibcode:2003PChem..64....3W. doi:10.1016/S0031-9422(03)00300-5. PMID 12946402.
Conner AH, Nagaoka M, Rowe JW, Perlman D (August 1976). "Microbial conversion of tall oil sterols to C19 steroids". Applied and Environmental Microbiology. 32 (2): 310–1. Bibcode:1976ApEnM..32..310C. doi:10.1128/AEM.32.2.310-311.1976. PMC 170056. PMID 987752.

ias.ac.in

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iupac.org

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"IUPAC-IUB Joint Commission on Biochemical Nomenclature (JCBN). The nomenclature of steroids. Recommendations 1989". Eur J Biochem. 186 (3): 430. 1989. doi:10.1111/j.1432-1033.1989.tb15228.x. PMID 2606099. p. 430: 3S‐1.0. Definition of steroids and sterols. Steroids are compounds possessing the skeleton of cyclopenta[a]phenanthrene or a skeleton derived therefrom by one or more bond scissions or ring expansions or contractions. Methyl groups are normally present at C-10 and C-13. An alkyl side chain may also be present at C-17. Sterols are steroids carrying a hydroxyl group at C-3 and most of the skeleton of cholestane.
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"IUPAC-IUB Joint Commission on Biochemical Nomenclature (JCBN). The nomenclature of steroids. Recommendations 1989". Eur J Biochem. 186 (3): 430. 1989. doi:10.1111/j.1432-1033.1989.tb15228.x. PMID 2606099. p. 430: 3S-1.1. Numbering and ring letters. Steroids are numbered and rings are lettered as in formula 1
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Silverthorn DU, Johnson BR, Ober WC, Ober CE, Silverthorn AC (2016). Human physiology : an integrated approach (Seventh ed.). [San Francisco]: Sinauer Associates; W.H. Freeman & Co. ISBN 978-0-321-98122-6. OCLC 890107246.
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Hanukoglu I (December 1992). "Steroidogenic enzymes: structure, function, and role in regulation of steroid hormone biosynthesis". The Journal of Steroid Biochemistry and Molecular Biology. 43 (8): 779–804. doi:10.1016/0960-0760(92)90307-5. PMID 22217824. S2CID 112729. Archived from the original on 26 April 2021. Retrieved 20 April 2018.