alpha-Cadinol

α-Cadinol

Names
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 (Jmol)	Interactive image
ChemSpider	8574094
PubChem	10398656
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]

See also

• δ-Cadinol (torreyol)
• t-Cadinol

References

1. 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.
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: 1. doi:10.1080/14786419.2011.653971. PMID 22273350.
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. PMID 22224304.
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. PMID 22224302.
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. PMID 22224295.
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. 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: 1. doi:10.1080/14786419.2011.636746. PMID 22115413.
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: 1. doi:10.1080/14786419.2011.636745. PMID 22103398.
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. 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. PMID 20714310.
14. 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