α-Cadinol

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
CAS Number	481-34-5 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:132905 ;
ChemSpider	8574094;
PubChem CID	10398656;
UNII	DC0YJ4816P ;
CompTox Dashboard (EPA)	DTXSID701017679 ;
	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; 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;
	SMILES CC1=C[C@H]2[C@@H](CC[C@@]([C@@H]2CC1)(C)O)C(C)C;
Properties
Chemical formula	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). Infobox references

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

Natural occurrence

This 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

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]

References

^ 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.
^ 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. 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; 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.
^ 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. 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.

[karin-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.

[herout-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.

[boligon-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.

[HoCL-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.

[escob-5] 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.

[freitas-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.

[muriel-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.

[lago-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.

[firozy-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.

[CJLiu-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.

[YYang-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.

[CLHo2-12] 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-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.

[TungYT-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.

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[9]

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[12]

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[14]

Natural occurrence

Biological activity

See also

References