Sclareolide: Difference between revisions

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Revision as of 13:05, 18 August 2023 editOAbot (talk \| contribs)Bots442,978 editsm Open access bot: doi updated in citation with #oabot.← Previous edit		Revision as of 22:03, 22 January 2024 edit undoMaxim Masiutin (talk \| contribs)Extended confirmed users, IP block exemptions, Pending changes reviewers31,087 edits Added s2cid.Next edit →
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	'''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 = }}</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>		'''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 ]<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.

Revision as of 22:03, 22 January 2024

Sclareolide
Names
Sclareolide
IUPAC name 3a,6,6,9a-tetramethyl-1,4,5,5a,7,8,9,9b-octahydronaphthofuran-2-one
Other names Norambreinolide
Identifiers
CAS Number	564-20-5
3D model (JSmol)	Interactive image
ChemSpider	809894
ECHA InfoCard	100.008.427
EC Number	209-269-0
PubChem CID	929262
UNII	37W4O0O6E6
CompTox Dashboard (EPA)	DTXSID8047686
InChI InChI=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/s1Key: IMKJGXCIJJXALX-SHUKQUCYSA-N 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/s1Key: IMKJGXCIJJXALX-SHUKQUCYBO
SMILES C12CCCC(1CC3(2CC(=O)O3)C)(C)C
Properties
Chemical formula	C₁₆H₂₆O₂
Molar mass	250.382 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). N verify (what is ?) Infobox references

Chemical compound

Sclareolide is a sesquiterpene lactone natural product derived from various plant sources including Salvia sclarea, Salvia yosgadensis, and cigar tobacco. It is a close analog of sclareol, a plant antifungal compound.

It is used as a fragrance in cosmetics and has been more recently marketed as a weight loss supplement, though there is no clinical evidence to support this effect.

References

Topcu, Guelacti; Ulubelen, Ayhan; Tam, Timothy Chit-Ming; Che, Chun-Tao (1996). "Norditerpenes and Norsesterterpenes from Salvia yosgadensis". Journal of Natural Products. 59 (2): 113–116. doi:10.1021/np960028h.
Kaneko, Hajime (1971). "Aroma of cigar tobacco. II. Isolation of norambreinolide from cigar tobacco". Agricultural and Biological Chemistry. 35 (9): 1461–1462. doi:10.1080/00021369.1971.10860098. S2CID 82467628.
Jasiński M; Stukkens Y; Degand H; Purnelle B; Marchand-Brynaert J; Boutry M (2001). "A Plant Plasma Membrane ATP Binding Cassette–Type Transporter Is Involved in Antifungal Terpenoid Secretion". Plant Cell. 13 (5): 1095–107. doi:10.1105/tpc.13.5.1095. PMC 135550. PMID 11340184.
Api, A.M.; et al. (2022). "RIFM fragrance ingredient safety assessment, sclareolide, CAS Registry Number 564-20-5". Food and Chemical Toxicology. 167: 113379. doi:10.1016/j.fct.2022.113379. PMID 35995076. S2CID 251696291.

Categories:

Revision as of 13:05, 18 August 2023 editOAbot (talk \| contribs)Bots442,978 editsm Open access bot: doi updated in citation with #oabot.← Previous edit		Revision as of 22:03, 22 January 2024 edit undoMaxim Masiutin (talk \| contribs)Extended confirmed users, IP block exemptions, Pending changes reviewers31,087 edits Added s2cid.Next edit →
Line 31:		Line 31:
	}}		}}

	'''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 = }}</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>		'''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 ]<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.