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Wikipedia

α-Cadinol

April 15, 2024

α-Cadinol or 10α-hydroxy-4-cadinene is an organic compound, a sesquiterpenoid alcohol.[1][2]

α-Cadinol
Names
IUPAC name
Cadin-4-en-10-ol
Systematic IUPAC name
(1R,4S,4aR,8aR)-1,6-Dimethyl-4-propan-2-yl-3,4,4a,7,8,8a-hexahydro-2H-naphthalen-1-ol
Identifiers
  • 481-34-5 Y
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:132905 Y
ChemSpider
  • 8574094
  • 10398656
UNII
  • DC0YJ4816P Y
  • InChI=1S/C15H26O/c1-10(2)12-7-8-15(4,16)14-6-5-11(3)9-13(12)14/h9-10,12-14,16H,5-8H2,1-4H3/t12-,13-,14+,15+/m0/s1
    Key: LHYHMMRYTDARSZ-BYNSBNAKSA-N
  • InChI=1/C15H26O/c1-10(2)12-7-8-15(4,16)14-6-5-11(3)9-13(12)14/h9-10,12-14,16H,5-8H2,1-4H3/t12-,13-,14+,15+/m0/s1
    Key: LHYHMMRYTDARSZ-BYNSBNAKBA
  • CC1=C[C@H]2[C@@H](CC[C@@]([C@@H]2CC1)(C)O)C(C)C
Properties
C
15H
26O
Molar mass 222.37 g/mol
Appearance white crystalline
Melting point 73 to 74 °C (163 to 165 °F; 346 to 347 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Natural occurrence edit

This compound is found in essential oils and extracts of many plants, such as

Biological activity edit

α-Cadinol was said to act as anti-fungal[12] and as hepatoprotective,[14] and was proposed as a possible remedy for drug-resistant tuberculosis.[5]

See also edit

References edit

  1. ^ Borg-Karlson, A (1981). "Configurations and conformations of torreyol (δ-cadinol), α-cadinol, T-muurolol and T-cadinol". Tetrahedron. 37 (22): 425–430. doi:10.1016/S0040-4020(01)92031-9.
  2. ^ V. Herout; V. Sýkora (1958). "The chemistry of cadinenes and cadinols". Tetrahedron. 4 (3–4): 246–255. doi:10.1016/0040-4020(58)80046-0.
  3. ^ Boligon, AA; Schwanz, TG; Piana, M; Bandeira, RV; Frohlich, JK; Brum, TF; Zadra, M; Athayde, ML (2012). "Chemical composition and antioxidant activity of the essential oil of Tabernaemontana catharinensis A. DC. Leaves". Natural Product Research. 27 (1): 68–71. doi:10.1080/14786419.2011.653971. PMID 22273350. S2CID 2230969.
  4. ^ Ho, CL; Liao, PC; Wang, EI; Su, YC (2011). "Composition and antimicrobial activity of the leaf and twig oils of Litsea acutivena from Taiwan". Natural Product Communications. 6 (11): 1755–8. doi:10.1177/1934578X1100601145. PMID 22224304.
  5. ^ a b Bueno, J; Escobar, P; Martínez, JR; Leal, SM; Stashenko, EE (2011). "Composition of three essential oils, and their mammalian cell toxicity and antimycobacterial activity against drug resistant-tuberculosis and nontuberculous mycobacteria strains". Natural Product Communications. 6 (11): 1743–8. doi:10.1177/1934578X1100601143. PMID 22224302. S2CID 30506397.
  6. ^ De Freitas, JG; Da Camara, CA; De Moraes, MM; Da Silva, HC (2011). "Volatile constituents of two species of Protium from the Atlantic rainforest in the state of Pernambuco, Brazil". Natural Product Communications. 6 (11): 1727–30. PMID 22224298.
  7. ^ Muriel, KA; Félix, TZ; Figueredo, G; Chalard, P; n'Guessan, YT (2011). "Essential oil of three Uvaria species from Ivory Coast". Natural Product Communications. 6 (11): 1715–8. doi:10.1177/1934578X1100601136. PMID 22224295. S2CID 23664205.
  8. ^ Lago, JH; Souza, ED; Mariane, B; Pascon, R; Vallim, MA; Martins, RC; Baroli, AA; Carvalho, BA; et al. (2011). "Chemical and biological evaluation of essential oils from two species of Myrtaceae - Eugenia uniflora L. And Plinia trunciflora (O. Berg) Kausel". Molecules (Basel, Switzerland). 16 (12): 9827–37. doi:10.3390/molecules16129827. PMC 6264170. PMID 22117172.
  9. ^ Firozy, M; Talebpour, Z; Sonboli, A (2011). "Essential oil composition and antioxidant activities of the various extracts of Tanacetum sonbolii Mozaff. (Asteraceae) from Iran". Natural Product Research. 26 (23): 2204–2207. doi:10.1080/14786419.2011.636746. PMID 22115413. S2CID 36405031.
  10. ^ Liu, CJ; Zhang, SQ; Zhang, JS; Liang, Q; Li, DS (2011). "Chemical composition and antioxidant activity of essential oil from berries of Schisandra chinensis (Turcz.) Baill". Natural Product Research. 26 (23): 2199–2203. doi:10.1080/14786419.2011.636745. PMID 22103398. S2CID 12460120.
  11. ^ Yang, Y; Xiao, Y; Liu, B; Fang, X; Yang, W; Xu, J (2011). "Comparison of headspace solid-phase microextraction with conventional extraction for the analysis of the volatile components in Melia azedarach". Talanta. 86: 356–61. doi:10.1016/j.talanta.2011.09.028. PMID 22063551.
  12. ^ a b Ho, CL; Liao, PC; Wang, EI; Su, YC (2011). "Composition and antifungal activities of the leaf essential oil of Neolitsea parvigemma from Taiwan". Natural Product Communications. 6 (9): 1357–60. PMID 21941915.
  13. ^ Z. C. Gazim; A. C. Amorim; A. M. Hovell; C. M. Rezende; I. A. Nascimento; G. A. Ferreira; D. A. Cortez (2010). "Seasonal variation, chemical composition, and analgesic and antimicrobial activities of the essential oil from leaves of Tetradenia riparia (Hochst.) Codd in southern Brazil". Molecules. 15 (8): 5509–5524. doi:10.3390/molecules15085509. PMC 6257709. PMID 20714310.
  14. ^ Tung, Y. T.; Huang, C. C.; Ho, S. T.; Kuo, Y. H.; Lin, C. C.; Lin, C. T.; Wu, J. H. (2011). "Bioactive phytochemicals of leaf essential oils of Cinnamomum osmophloeum prevent lipopolysaccharide/D-galactosamine (LPS/D-GalN)-induced acute hepatitis in mice". J. Agric. Food Chem. 59 (15): 8117–8123. doi:10.1080/10412905.1999.9712005. PMID 21699244.

April 15, 2024
cadinol, 10α, hydroxy, cadinene, organic, compound, sesquiterpenoid, alcohol, namesiupac, name, cadin, olsystematic, iupac, name, dimethyl, propan, hexahydro, naphthalen, olidentifierscas, number, model, jsmol, interactive, imagechebi, chebi, 132905, ychemspid. a Cadinol or 10a hydroxy 4 cadinene is an organic compound a sesquiterpenoid alcohol 1 2 a Cadinol NamesIUPAC name Cadin 4 en 10 olSystematic IUPAC name 1R 4S 4aR 8aR 1 6 Dimethyl 4 propan 2 yl 3 4 4a 7 8 8a hexahydro 2H naphthalen 1 olIdentifiersCAS Number 481 34 5 Y3D model JSmol Interactive imageChEBI CHEBI 132905 YChemSpider 8574094PubChem CID 10398656UNII DC0YJ4816P YInChI InChI 1S C15H26O c1 10 2 12 7 8 15 4 16 14 6 5 11 3 9 13 12 14 h9 10 12 14 16H 5 8H2 1 4H3 t12 13 14 15 m0 s1Key LHYHMMRYTDARSZ BYNSBNAKSA NInChI 1 C15H26O c1 10 2 12 7 8 15 4 16 14 6 5 11 3 9 13 12 14 h9 10 12 14 16H 5 8H2 1 4H3 t12 13 14 15 m0 s1Key LHYHMMRYTDARSZ BYNSBNAKBASMILES CC1 C C H 2 C H CC C C H 2CC1 C O C C CPropertiesChemical formula C15 H26 OMolar mass 222 37 g molAppearance white crystallineMelting point 73 to 74 C 163 to 165 F 346 to 347 K Except where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa Infobox references Contents 1 Natural occurrence 2 Biological activity 3 See also 4 ReferencesNatural occurrence editThis compound is found in essential oils and extracts of many plants such as Agrotaxis selaginoides Tabernaemontana catharinensis 3 Litsea acutivena 7 7 4 Salvia aratocensis 20 5 Protium giganteum 7 6 Uvaria ovata root bark 13 24 7 Plinia trunciflora 19 8 Tanacetum sonbolii 35 9 Schisandra chinensis berries 5 10 Melia azedarach 11 11 Neolitsea parvigemma 10 12 Tetradenia riparia 8 13 Biological activity edita Cadinol was said to act as anti fungal 12 and as hepatoprotective 14 and was proposed as a possible remedy for drug resistant tuberculosis 5 See also editd Cadinol torreyol References edit Borg Karlson A 1981 Configurations and conformations of torreyol d cadinol a cadinol T muurolol and T cadinol Tetrahedron 37 22 425 430 doi 10 1016 S0040 4020 01 92031 9 V Herout V Sykora 1958 The chemistry of cadinenes and cadinols Tetrahedron 4 3 4 246 255 doi 10 1016 0040 4020 58 80046 0 Boligon AA Schwanz TG Piana M Bandeira RV Frohlich JK Brum TF Zadra M Athayde ML 2012 Chemical composition and antioxidant activity of the essential oil of Tabernaemontana catharinensis A DC Leaves Natural Product Research 27 1 68 71 doi 10 1080 14786419 2011 653971 PMID 22273350 S2CID 2230969 Ho CL Liao PC Wang EI Su YC 2011 Composition and antimicrobial activity of the leaf and twig oils of Litsea acutivena from Taiwan Natural Product Communications 6 11 1755 8 doi 10 1177 1934578X1100601145 PMID 22224304 a b Bueno J Escobar P Martinez JR Leal SM Stashenko EE 2011 Composition of three essential oils and their mammalian cell toxicity and antimycobacterial activity against drug resistant tuberculosis and nontuberculous mycobacteria strains Natural Product Communications 6 11 1743 8 doi 10 1177 1934578X1100601143 PMID 22224302 S2CID 30506397 De Freitas JG Da Camara CA De Moraes MM Da Silva HC 2011 Volatile constituents of two species of Protium from the Atlantic rainforest in the state of Pernambuco Brazil Natural Product Communications 6 11 1727 30 PMID 22224298 Muriel KA Felix TZ Figueredo G Chalard P n Guessan YT 2011 Essential oil of three Uvaria species from Ivory Coast Natural Product Communications 6 11 1715 8 doi 10 1177 1934578X1100601136 PMID 22224295 S2CID 23664205 Lago JH Souza ED Mariane B Pascon R Vallim MA Martins RC Baroli AA Carvalho BA et al 2011 Chemical and biological evaluation of essential oils from two species of Myrtaceae Eugenia uniflora L And Plinia trunciflora O Berg Kausel Molecules Basel Switzerland 16 12 9827 37 doi 10 3390 molecules16129827 PMC 6264170 PMID 22117172 Firozy M Talebpour Z Sonboli A 2011 Essential oil composition and antioxidant activities of the various extracts of Tanacetum sonbolii Mozaff Asteraceae from Iran Natural Product Research 26 23 2204 2207 doi 10 1080 14786419 2011 636746 PMID 22115413 S2CID 36405031 Liu CJ Zhang SQ Zhang JS Liang Q Li DS 2011 Chemical composition and antioxidant activity of essential oil from berries of Schisandra chinensis Turcz Baill Natural Product Research 26 23 2199 2203 doi 10 1080 14786419 2011 636745 PMID 22103398 S2CID 12460120 Yang Y Xiao Y Liu B Fang X Yang W Xu J 2011 Comparison of headspace solid phase microextraction with conventional extraction for the analysis of the volatile components in Melia azedarach Talanta 86 356 61 doi 10 1016 j talanta 2011 09 028 PMID 22063551 a b Ho CL Liao PC Wang EI Su YC 2011 Composition and antifungal activities of the leaf essential oil of Neolitsea parvigemma from Taiwan Natural Product Communications 6 9 1357 60 PMID 21941915 Z C Gazim A C Amorim A M Hovell C M Rezende I A Nascimento G A Ferreira D A Cortez 2010 Seasonal variation chemical composition and analgesic and antimicrobial activities of the essential oil from leaves of Tetradenia riparia Hochst Codd in southern Brazil Molecules 15 8 5509 5524 doi 10 3390 molecules15085509 PMC 6257709 PMID 20714310 Tung Y T Huang C C Ho S T Kuo Y H Lin C C Lin C T Wu J H 2011 Bioactive phytochemicals of leaf essential oils of Cinnamomum osmophloeum prevent lipopolysaccharide D galactosamine LPS D GalN induced acute hepatitis in mice J Agric Food Chem 59 15 8117 8123 doi 10 1080 10412905 1999 9712005 PMID 21699244 Retrieved from https en wikipedia org w index php title A Cadinol amp oldid 1170209739, wikipedia, wiki, book, books, library,

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