Alpha-Cadinol

α-Cadinol
Nombre IUPAC
	(1R,4S,4aR,8aR)-1,6-Dimethyl-4-propan-2-yl-3,4,4a,7,8,8a-hexahydro-2H-naphthalen-1-ol
General
Fórmula estructural
Fórmula molecular	?
Identificadores
Número CAS	481-34-5
ChEBI	132905
ChEMBL	CHEMBL486795
ChemSpider	8574094
PubChem	10398656
UNII	DC0YJ4816P
	SMILES CC1=C[C@H]2[C@@H](CC[C@@]([C@@H]2CC1)(C)O)C(C)C
	InChI 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
Propiedades físicas
Apariencia	blanco cristalino
Masa molar	222,37 g/mol
Punto de fusión	74 °C (347 K)
	Valores en el SI y en condiciones estándar; (25 ℃ y 1 atm), salvo que se indique lo contrario.
	[editar datos en Wikidata]

α-Cadinol o 10α-hydroxy-4-cadinene es un compuesto orgánico, un sesquiterpenoide de alcohol.^[2]^[3]

Presencia natural

Este compuesto se encuentra en aceites esenciales y extractos de muchas plantas, tales como:

Agrotaxis selaginoides,
Tabernaemontana catharinensis^[4]
Litsea acutivena (7.7%),^[5]
Salvia aratocensis (20%),^[6]
Protium giganteum (7%),^[7]
Uvaria ovata root bark (13–24%),^[8]
Plinia trunciflora (19%)^[9]
Tanacetum sonbolii (35%)^[10]
Schisandra chinensis berries (5%),^[11]
Melia azedarach (11%),^[12]
Neolitsea parvigemma (10%),^[13]
Tetradenia riparia (8%)^[14]

Actividad biológica

α-Cadinol se dice que actúa como antifúngica^[13] y como hepatoprotector,^[15] y fue propuesto como un posible remedio para la resistencia a los medicamentos de la tuberculosis.^[6]

Referencias

↑ Número CAS
↑ Borg-Karlson, A (1981). «Configurations and conformations of torreyol (δ-cadinol), α-cadinol, T-muurolol and T-cadinol». Tetrahedron 37 (22): 425. doi:10.1016/S0040-4020(01)92031-9.
↑ 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.
↑ 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: 1. PMID 22273350. doi:10.1080/14786419.2011.653971.
↑ 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. PMID 22224304.
↑ ^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. PMID 22224302.
↑ 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; 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. PMID 22224295.
↑ 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. PMID 22117172. doi:10.3390/molecules16129827.
↑ 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: 1. PMID 22115413. doi:10.1080/14786419.2011.636746.
↑ 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: 1. PMID 22103398. doi:10.1080/14786419.2011.636745.
↑ 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. PMID 22063551. doi:10.1016/j.talanta.2011.09.028.
↑ ^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. PMID 20714310. doi:10.3390/molecules15085509.
↑ Y. T. Tung, C. C. Huang, S. T. Ho, Y. H. Kuo, C. C. Lin, C. T. Lin, J. H. Wu (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. volume 59 issue 15 pages 8117-8123. doi 10.1080/10412905.1999.9712005

Enlaces externos

Esta obra contiene una traducción derivada de «Alpha-Cadinol» de Wikipedia en inglés, publicada por sus editores bajo la Licencia de documentación libre de GNU y la Licencia Creative Commons Atribución-CompartirIgual 4.0 Internacional.

Datos: Q4734900

[1] Número CAS

[karin-2] Borg-Karlson, A (1981). «Configurations and conformations of torreyol (δ-cadinol), α-cadinol, T-muurolol and T-cadinol». Tetrahedron 37 (22): 425. doi:10.1016/S0040-4020(01)92031-9.

[herout-3] 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.

[boligon-4] 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: 1. PMID 22273350. doi:10.1080/14786419.2011.653971.

[HoCL-5] 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. PMID 22224304.

[escob-6] 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. PMID 22224302.

[freitas-7] 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-8] 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. PMID 22224295.

[lago-9] 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. PMID 22117172. doi:10.3390/molecules16129827.

[firozy-10] 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: 1. PMID 22115413. doi:10.1080/14786419.2011.636746.

[CJLiu-11] 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: 1. PMID 22103398. doi:10.1080/14786419.2011.636745.

[YYang-12] 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. PMID 22063551. doi:10.1016/j.talanta.2011.09.028.

[CLHo2-13] 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.

[Gazim-14] 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. PMID 20714310. doi:10.3390/molecules15085509.

[TungYT-15] Y. T. Tung, C. C. Huang, S. T. Ho, Y. H. Kuo, C. C. Lin, C. T. Lin, J. H. Wu (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. volume 59 issue 15 pages 8117-8123. doi 10.1080/10412905.1999.9712005

[2]

[3]

[1]

[4]

[5]

[6]

[7]

[8]

[9]

[10]

[11]

[12]

[13]

[14]

[15]