Α-Cadinol

{{lowercase title}} {{Chembox | Name =α-Cadinol | ImageFile =Alpha-Cadinol.svg | ImageSize = | ImageAlt = | IUPACName = Cadin-4-en-10-ol | SystematicName =(1''R'',4''S'',4a''R'',8a''R'')-1,6-Dimethyl-4-propan-2-yl-3,4,4a,7,8,8a-hexahydro-2''H''-naphthalen-1-ol | OtherNames = |Section1={{Chembox Identifiers | CASNo =481-34-5 | CASNo_Ref = {{cascite|correct|CAS}} | UNII_Ref = {{fdacite|correct|FDA}} | UNII = DC0YJ4816P | PubChem =10398656 | SMILES = CC1=C[C@H]2[C@@H](CC[C@@]([C@@H]2CC1)(C)O)C(C)C | ChemSpiderID = 8574094 | ChEBI_Ref = {{ebicite|correct|EBI}} | ChEBI = 132905 | 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 | InChIKey = LHYHMMRYTDARSZ-BYNSBNAKBA | StdInChI = 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 | StdInChIKey = LHYHMMRYTDARSZ-BYNSBNAKSA-N}} |Section2={{Chembox Properties | Formula ={{chem|C|15|H|26|O}} | MolarMass =222.37 g/mol | Appearance =white crystalline | Density = | MeltingPtC = 73 to 74 | MeltingPt_notes = | BoilingPt = | Solubility = }} |Section3={{Chembox Hazards | MainHazards = | FlashPt = | AutoignitionPt = }} }}

'''α-Cadinol''' or '''10α-hydroxy-4-cadinene''' is an organic compound, a sesquiterpenoid alcohol.<ref name=karin>{{cite journal | doi = 10.1016/S0040-4020(01)92031-9 | title = Configurations and conformations of torreyol (δ-cadinol), α-cadinol, T-muurolol and T-cadinol | year = 1981 | last1 = Borg-Karlson | first1 = A | journal = Tetrahedron | volume = 37 | issue = 22 | pages = 425–430}}</ref><ref name=herout>{{cite journal |author1=V. Herout |author2=V. Sýkora | year = 1958 | title = The chemistry of cadinenes and cadinols | journal = Tetrahedron | volume = 4 | pages = 246–255 | doi = 10.1016/0040-4020(58)80046-0 | issue = 3–4}}</ref>

==Natural occurrence== This compound is found in essential oils and extracts of many plants, such as *''Agrotaxis selaginoides'', * ''Tabernaemontana catharinensis''<ref name=boligon>{{cite journal | pmid = 22273350 | year = 2012 | last1 = Boligon | first1 = AA | last2 = Schwanz | first2 = TG | last3 = Piana | first3 = M | last4 = Bandeira | first4 = RV | last5 = Frohlich | first5 = JK | last6 = Brum | first6 = TF | last7 = Zadra | first7 = M | last8 = Athayde | first8 = ML | title = Chemical composition and antioxidant activity of the essential oil of ''Tabernaemontana catharinensis'' A. DC. Leaves | doi = 10.1080/14786419.2011.653971 | journal = Natural Product Research | pages = 68–71 | volume=27| issue = 1 | s2cid = 2230969 }}</ref> * ''Litsea acutivena'' (7.7%),<ref name=HoCL>{{cite journal | pmid = 22224304 | year = 2011 | last1 = Ho | first1 = CL | last2 = Liao | first2 = PC | last3 = Wang | first3 = EI | last4 = Su | first4 = YC | title = Composition and antimicrobial activity of the leaf and twig oils of ''Litsea acutivena'' from Taiwan | volume = 6 | issue = 11 | pages = 1755–8 | journal = Natural Product Communications| doi = 10.1177/1934578X1100601145| doi-access = free }}</ref> * ''Salvia aratocensis'' (20%),<ref name=escob>{{cite journal | pmid = 22224302 | year = 2011 | last1 = Bueno | first1 = J | last2 = Escobar | first2 = P | last3 = Martínez | first3 = JR | last4 = Leal | first4 = SM | last5 = Stashenko | first5 = EE | title = Composition of three essential oils, and their mammalian cell toxicity and antimycobacterial activity against drug resistant-tuberculosis and nontuberculous mycobacteria strains | volume = 6 | issue = 11 | pages = 1743–8 | journal = Natural Product Communications| doi = 10.1177/1934578X1100601143 | s2cid = 30506397 | doi-access = free }}</ref> * ''Protium giganteum'' (7%),<ref name=freitas>{{cite journal | pmid = 22224298 | year = 2011 | last1 = De Freitas | first1 = JG | last2 = Da Camara | first2 = CA | last3 = De Moraes | first3 = MM | last4 = Da Silva | first4 = HC | title = Volatile constituents of two species of ''Protium'' from the Atlantic rainforest in the state of Pernambuco, Brazil | volume = 6 | issue = 11 | pages = 1727–30 | journal = Natural Product Communications}}</ref> * ''Uvaria ovata'' root bark (13–24%),<ref name=muriel>{{cite journal | pmid = 22224295 | year = 2011 | last1 = Muriel | first1 = KA | last2 = Félix | first2 = TZ | last3 = Figueredo | first3 = G | last4 = Chalard | first4 = P | last5 = n'Guessan | first5 = YT | title = Essential oil of three ''Uvaria'' species from Ivory Coast | volume = 6 | issue = 11 | pages = 1715–8 | journal = Natural Product Communications| doi = 10.1177/1934578X1100601136 | s2cid = 23664205 | doi-access = free }}</ref> * ''Plinia trunciflora'' (19%)<ref name=lago>{{cite journal | pmid = 22117172 | year = 2011 | last1 = Lago | first1 = JH | last2 = Souza | first2 = ED | last3 = Mariane | first3 = B | last4 = Pascon | first4 = R | last5 = Vallim | first5 = MA | last6 = Martins | first6 = RC | last7 = Baroli | first7 = AA | last8 = Carvalho | first8 = BA | last9 = Soares | first9 = MG | display-authors=8| title = Chemical and biological evaluation of essential oils from two species of Myrtaceae - ''Eugenia uniflora'' L. And ''Plinia trunciflora'' (O. Berg) Kausel | volume = 16 | issue = 12 | pages = 9827–37 | pmc=6264170 | doi = 10.3390/molecules16129827 | journal = Molecules (Basel, Switzerland)| doi-access = free }}</ref> * ''Tanacetum sonbolii'' (35%)<ref name=firozy>{{cite journal | pmid = 22115413 | year = 2011 | last1 = Firozy | first1 = M | last2 = Talebpour | first2 = Z | last3 = Sonboli | first3 = A | title = Essential oil composition and antioxidant activities of the various extracts of ''Tanacetum sonbolii'' Mozaff. (Asteraceae) from Iran | doi = 10.1080/14786419.2011.636746 | journal = Natural Product Research | pages = 2204–2207 | volume=26| issue = 23 | s2cid = 36405031 }}</ref> * ''Schisandra chinensis'' berries (5%),<ref name=CJLiu>{{cite journal | pmid = 22103398 | year = 2011 | last1 = Liu | first1 = CJ | last2 = Zhang | first2 = SQ | last3 = Zhang | first3 = JS | last4 = Liang | first4 = Q | last5 = Li | first5 = DS | title = Chemical composition and antioxidant activity of essential oil from berries of ''Schisandra chinensis'' (Turcz.) Baill | doi = 10.1080/14786419.2011.636745 | journal = Natural Product Research | pages = 2199–2203 | volume=26| issue = 23 | s2cid = 12460120 }}</ref> * ''Melia azedarach'' (11%),<ref name=YYang>{{cite journal | pmid = 22063551 | year = 2011 | last1 = Yang | first1 = Y | last2 = Xiao | first2 = Y | last3 = Liu | first3 = B | last4 = Fang | first4 = X | last5 = Yang | first5 = W | last6 = Xu | first6 = J | title = Comparison of headspace solid-phase microextraction with conventional extraction for the analysis of the volatile components in ''Melia azedarach'' | volume = 86 | pages = 356–61 | doi = 10.1016/j.talanta.2011.09.028 | journal = Talanta}}</ref> * ''Neolitsea parvigemma'' (10%),<ref name=CLHo2>{{cite journal | pmid = 21941915 | year = 2011 | last1 = Ho | first1 = CL | last2 = Liao | first2 = PC | last3 = Wang | first3 = EI | last4 = Su | first4 = YC | title = Composition and antifungal activities of the leaf essential oil of ''Neolitsea parvigemma'' from Taiwan | volume = 6 | issue = 9 | pages = 1357–60 | journal = Natural Product Communications}}</ref> * ''Tetradenia riparia'' (8%)<ref name=Gazim>{{cite journal |author1=Z. C. Gazim |author2=A. C. Amorim |author3=A. M. Hovell |author4=C. M. Rezende |author5=I. A. Nascimento |author6=G. A. Ferreira |author7=D. A. Cortez | year = 2010 | title = Seasonal variation, chemical composition, and analgesic and antimicrobial activities of the essential oil from leaves of ''Tetradenia riparia'' (Hochst.) Codd in southern Brazil | journal = Molecules | volume = 15 | issue = 8 | pages = 5509–5524 | pmc=6257709|doi = 10.3390/molecules15085509 | pmid = 20714310| doi-access = free }}</ref>

==Biological activity== α-Cadinol was said to act as anti-fungal<ref name=CLHo2/> and as hepatoprotective,<ref name=TungYT>{{cite journal | last1 = Tung | first1 = Y. T. | last2 = Huang | first2 = C. C. | last3 = Ho | first3 = S. T. | last4 = Kuo | first4 = Y. H. | last5 = Lin | first5 = C. C. | last6 = Lin | first6 = C. T. | last7 = Wu | first7 = J. H. | year = 2011 | title = Bioactive phytochemicals of leaf essential oils of ''Cinnamomum osmophloeum'' prevent lipopolysaccharide/D-galactosamine (LPS/D-GalN)-induced acute hepatitis in mice | journal = J. Agric. Food Chem. | volume = 59 | issue = 15 | pages = 8117–8123 | doi = 10.1080/10412905.1999.9712005 | pmid = 21699244 }}</ref> and was proposed as a possible remedy for drug-resistant tuberculosis.<ref name=escob/>

==See also== * δ-Cadinol (torreyol)

==References== {{reflist}}

{{DEFAULTSORT:Cadinol, alpha-}} Category:Sesquiterpenes Category:Tertiary alcohols Category:Alkene derivatives Category:Isopropyl compounds