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Revision as of 22:27, 11 October 2011 editCheMoBot (talk | contribs)Bots141,565 edits Updating {{chembox}} (no changed fields - added verified revid - updated 'ChemSpiderID_Ref', 'DrugBank_Ref', 'ChEMBL_Ref', 'ChEBI_Ref', 'KEGG_Ref', 'StdInChI_Ref', 'StdInChIKey_Ref', 'ChEBI_Ref') per Chem/Drugbox validation (repor...← Previous edit Latest revision as of 22:03, 22 January 2024 edit undoMaxim Masiutin (talk | contribs)Extended confirmed users, IP block exemptions, Pending changes reviewers31,043 edits Added s2cid. 
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{{chembox {{chembox
| Verifiedfields = changed
⚫ | verifiedrevid = 444099250
| Watchedfields = changed
⚫ | Name = Sclareolide
⚫ | verifiedrevid = 455114494
| ImageFile = Sclareolide structure.png
⚫ | Name = Sclareolide
| ImageSize = 200px
| ImageName = Sclareolide | ImageFile = Sclareolide.svg
| ImageSize = 200px
⚫ | IUPACName = 3a,6,6,9a-tetramethyl-1,4,5,5a,7,8,9,9b-octahydronaphthofuran-2-one
| ImageName = Sclareolide
⚫ | OtherNames = Norambreinolide
⚫ | IUPACName = 3a,6,6,9a-tetramethyl-1,4,5,5a,7,8,9,9b-octahydronaphthofuran-2-one
⚫ | Section1 = {{Chembox Identifiers
⚫ | OtherNames = Norambreinolide
⚫ | CASNo = 564-20-5
⚫ | Section1 = {{Chembox Identifiers
⚫ | PubChem = 61129
| CASNo_Ref = {{cascite|correct|??}}
⚫ | CASNo = 564-20-5
| EINECS = 209-269-0
⚫ | PubChem = 929262
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID = 809894
⚫ | SMILES = C12CCCC(1CC3(2CC(=O)O3)C)(C)C
| InChI = 1/C16H26O2/c1-14(2)7-5-8-15(3)11(14)6-9-16(4)12(15)10-13(17)18-16/h11-12H,5-10H2,1-4H3/t11-,12+,15-,16+/m0/s1
| InChIKey = IMKJGXCIJJXALX-SHUKQUCYBO
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| StdInChI = 1S/C16H26O2/c1-14(2)7-5-8-15(3)11(14)6-9-16(4)12(15)10-13(17)18-16/h11-12H,5-10H2,1-4H3/t11-,12+,15-,16+/m0/s1
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
| StdInChIKey = IMKJGXCIJJXALX-SHUKQUCYSA-N
| UNII_Ref = {{fdacite|correct|FDA}} | UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 37W4O0O6E6 | UNII = 37W4O0O6E6
⚫ | SMILES = C12(CC(O2)=O)()3(C)CCCC(C)(C)3()CC1
}} }}
| Section2 = {{Chembox Properties | Section2 = {{Chembox Properties
| C=16|H=26|O=2 | C=16|H=26|O=2
}} }}
}} }}


'''Sclareolide''' is a ] natural product derived from various plant sources including '']'', '']'',<ref>{{cite journal | title = Norditerpenes and Norsesterterpenes from Salvia yosgadensis | author = Topcu, Guelacti; Ulubelen, Ayhan; Tam, Timothy Chit-Ming; Che, Chun-Tao | journal = ] | year = 1996 | volume = 59 | issue = 2 | pages = 113–116 | doi = 10.1021/np960028h}}</ref> and cigar tobacco.<ref>{{cite journal | author = Kaneko, Hajime | title = Aroma of cigar tobacco. II. Isolation of norambreinolide from cigar tobacco | journal = Agricultural and Biological Chemistry | year = 1971 | volume = 35 | issue = 9 | pages = 1461–1462}}</ref> It is a close analog of ], a plant antifungal compound.<ref>{{cite journal |author=Jasiński M, Stukkens Y, Degand H, Purnelle B, Marchand-Brynaert J, Boutry M |title=A plant plasma membrane ATP binding cassette-type transporter is involved in antifungal terpenoid secretion |journal=Plant Cell |volume=13 |issue=5 |pages=1095–107 |year=2001 |pmid=11340184 |doi=10.1105/tpc.13.5.1095 |pmc=135550}}</ref> '''Sclareolide''' is a ] natural product derived from various plant sources including '']'', '']'',<ref>{{cite journal | title = Norditerpenes and Norsesterterpenes from Salvia yosgadensis |author1=Topcu, Guelacti |author2=Ulubelen, Ayhan |authorlink2=Ayhan Ulubelen |author3=Tam, Timothy Chit-Ming |author4=Che, Chun-Tao | journal = ] | year = 1996 | volume = 59 | issue = 2 | pages = 113–116 | doi = 10.1021/np960028h}}</ref> and cigar tobacco.<ref>{{cite journal | author = Kaneko, Hajime | title = Aroma of cigar tobacco. II. Isolation of norambreinolide from cigar tobacco | journal = Agricultural and Biological Chemistry | year = 1971 | volume = 35 | issue = 9 | pages = 1461–1462| doi = 10.1080/00021369.1971.10860098 | doi-access = | s2cid = 82467628 }}</ref> It is a close analog of ], a plant antifungal compound.<ref>{{cite journal |author1=Jasiński M |author2=Stukkens Y |author3=Degand H |author4=Purnelle B |author5=Marchand-Brynaert J |author6=Boutry M |title=A Plant Plasma Membrane ATP Binding Cassette–Type Transporter Is Involved in Antifungal Terpenoid Secretion |journal=Plant Cell |volume=13 |issue=5 |pages=1095–107 |year=2001 |pmid=11340184 |doi=10.1105/tpc.13.5.1095 |pmc=135550}}</ref>


It is used as a fragrance in ]<ref>{{cite journal | doi = 10.1016/j.fct.2022.113379 | title = RIFM fragrance ingredient safety assessment, sclareolide, CAS Registry Number 564-20-5 | year = 2022 | last1 = Api | first1 = A.M. | last2 = Belsito | first2 = D. | last3 = Botelho | first3 = D. | last4 = Bruze | first4 = M. | last5 = Burton | first5 = G.A. | last6 = Cancellieri | first6 = M.A. | last7 = Chon | first7 = H. | last8 = Dagli | first8 = M.L. | last9 = Date | first9 = M. | last10 = Dekant | first10 = W. | last11 = Deodhar | first11 = C. | last12 = Fryer | first12 = A.D. | last13 = Jones | first13 = L. | last14 = Joshi | first14 = K. | last15 = Kumar | first15 = M. | last16 = Lapczynski | first16 = A. | last17 = Lavelle | first17 = M. | last18 = Lee | first18 = I. | last19 = Liebler | first19 = D.C. | last20 = Moustakas | first20 = H. | last21 = Na | first21 = M. | last22 = Penning | first22 = T.M. | last23 = Ritacco | first23 = G. | last24 = Romine | first24 = J. | last25 = Sadekar | first25 = N. | last26 = Schultz | first26 = T.W. | last27 = Selechnik | first27 = D. | last28 = Siddiqi | first28 = F. | last29 = Sipes | first29 = I.G. | last30 = Sullivan | first30 = G. | journal = Food and Chemical Toxicology | volume = 167 | page = 113379 | pmid = 35995076 | s2cid = 251696291 | display-authors = 1 }}</ref> and has been more recently marketed as a weight loss supplement, though there is no clinical evidence to support this effect.
It is used as a fragrance in ] and has been more recently marketed as a weight loss supplement, though there is no clinical evidence to support this effect.

The company WILD believes and presumably tries to use sclareolide to hypothetically block the perception of "off" flavors in potassium chloride when used as a table salt substitute.<ref>http://www.wildflavors.com/index.cfm?fuseaction=news.item&newsCategoryID=B57723F5-CF1C-2465-18BFD630DB5F7B15&newsItemID=F75F69F9-AF3A-F845-BB676985C8D284E2</ref>


==References== ==References==
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