| Revision as of 09:02, 9 April 2010 editحسن علي البط (talk | contribs)Extended confirmed users, Pending changes reviewers19,940 editsm Removed Category:Terpenes and terpenoids; Adding category Category:Sesquiterpenes (using HotCat)← Previous edit |
Latest revision as of 22:45, 12 November 2024 edit undoBruce1ee (talk | contribs)Autopatrolled, Extended confirmed users, Pending changes reviewers, Rollbackers269,738 editsm fixed lint errors – invalid file options |
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{{chembox |
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{{chembox |
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| Verifiedfields = changed |
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| verifiedrevid = 288107412 |
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| Watchedfields = changed |
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| Reference=<ref name="Merck">'']'', 11th Edition, '''6388'''.</ref> |
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| verifiedrevid = 354914448 |
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| Name = ''trans''-Nerolidol <small>(top)</small> and ''cis''-Nerolidol <small>(bottom)</small> |
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| Reference =<ref name="Merck">'']'', 11th Edition, '''6388'''.</ref> |
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| ImageFile1 = Nerolidol.png |
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| Name = ''trans''-Nerolidol <small>(top)</small> and ''cis''-Nerolidol <small>(bottom)</small> |
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| ImageSize1 = 200px |
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| ImageName1 = ''trans''-Nerolidol |
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| ImageFile1 = Nerolidol.png |
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| ImageSize1 = |
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| ImageFile2 = Nerolidol - cis.png |
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| ImageName1 = ''trans''-Nerolidol |
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| ImageSize2 = 200px |
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| ImageFile2 = Nerolidol - cis.png |
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| ImageName2 = ''cis''-Nerolidol |
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| ImageSize2 = |
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| IUPACName = 3,7,11-Trimethyl-1,6,10-dodecatrien-3-ol |
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| ImageName2 = ''cis''-Nerolidol |
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| OtherNames = Peruviol |
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| IUPACName = 3,7,11-Trimethyl-1,6,10-dodecatrien-3-ol |
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| Section1 = {{Chembox Identifiers |
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| OtherNames = Peruviol |
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| CASNo_Ref = {{cascite}} |
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|Section1={{Chembox Identifiers |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo = 7212-44-4 |
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| CASNo = 7212-44-4 |
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| CASOther = (unspecified)<br> (''cis'')<br /> (''trans'') |
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| CASNo_Comment = (unspecified) |
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| CASNo1_Ref = {{cascite|correct|CAS}} |
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| SMILES = CC(C)=CCCC(C)=CCCC(C)(O)C=C |
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| CASNo1 = 3790-78-1 |
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| CASNo1_Comment = (6-''Z'') |
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| CASNo2_Ref = {{cascite|correct|CAS}} |
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| CASNo2 = 40716-66-3 |
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| CASNo2_Comment = (6-''E'') |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = QR6IP857S6 |
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| UNII_Comment = (unspecified) |
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| UNII1_Ref = {{fdacite|correct|FDA}} |
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| UNII1 = 81K23DEF7B |
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| UNII1_Comment = (''cis'') |
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| UNII2_Ref = {{fdacite|correct|FDA}} |
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| UNII2 = FG5V0N8P2H |
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| UNII2_Comment = (''trans'') |
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| PubChem = 8888 |
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| PubChem_Comment = (unspecified) |
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| PubChem1 = 5320128 |
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| PubChem1_Comment = (''cis'') |
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| PubChem2 = 5284507 |
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| PubChem2_Comment = (''trans'') |
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| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} |
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| ChemSpiderID = 8549 |
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| ChemSpiderID_Comment = (unspecified) |
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| ChemSpiderID1_Ref = {{chemspidercite|changed|chemspider}} |
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| ChemSpiderID1 = 4478283 |
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| ChemSpiderID1_Comment = (''cis'') |
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| ChemSpiderID2_Ref = {{chemspidercite|changed|chemspider}} |
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| ChemSpiderID2 = 4447568 |
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| ChemSpiderID2_Comment = (''trans'') |
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| ChEBI = 7524 |
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| ChEBI_Comment = (unspecified) |
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| ChEBI1 = 173119 |
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| ChEBI1_Comment = (''cis'') |
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| ChEBI2 = 141283 |
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| ChEBI2_Comment = (''trans'') |
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| SMILES = OC(\C=C)(CCC=C(CC/C=C(\C)C)C)C |
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| SMILES_Comment = (unspecified) |
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| SMILES1 = OC(\C=C)(CC\C=C(/CC/C=C(\C)C)C)C |
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| SMILES1_Comment = (''cis'') |
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| SMILES2 = CC(=CCC/C(=C/CCC(C)(C=C)O)/C)C |
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| SMILES2_Comment = (''trans'') |
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| InChI = 1S/C15H26O/c1-6-15(5,16)12-8-11-14(4)10-7-9-13(2)3/h6,9,11,16H,1,7-8,10,12H2,2-5H3 |
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| InChI_Comment = (unspecified) |
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| InChIKey = FQTLCLSUCSAZDY-UHFFFAOYSA-N |
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| InChI1 = 1S/C15H26O/c1-6-15(5,16)12-8-11-14(4)10-7-9-13(2)3/h6,9,11,16H,1,7-8,10,12H2,2-5H3/b14-11- |
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| InChI1_Comment = (''cis'') |
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| InChIKey1 = FQTLCLSUCSAZDY-KAMYIIQDSA-N |
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| InChI2 = 1S/C15H26O/c1-6-15(5,16)12-8-11-14(4)10-7-9-13(2)3/h6,9,11,16H,1,7-8,10,12H2,2-5H3/b14-11+ |
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| InChI2_Comment = (''trans'') |
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| InChIKey2 = FQTLCLSUCSAZDY-SDNWHVSQSA-N |
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}} |
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| Section2 = {{Chembox Properties |
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|Section2={{Chembox Properties |
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|RefractIndex= 1.4898 |
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| Formula = C<sub>15</sub>H<sub>26</sub>O |
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| Formula = C<sub>15</sub>H<sub>26</sub>O |
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| MolarMass = 222.37 g/mol |
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| Density = 0.872 g/cm<sup>3</sup> |
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| MolarMass = 222.37 g/mol |
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| Density = 0.872 g/cm<sup>3</sup> |
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| MeltingPt = |
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| MeltingPt = |
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| BoilingPt = 122 °C at 3 mmHg |
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| BoilingPtC = 122 |
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| BoilingPt_notes = at 3 mmHg |
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'''Nerolidol''', also known as peruviol, is a naturally occurring ] found in the ]s of many types of plants and flowers.<ref name="Merck"/> There are two ]s of nerolidol, ''cis'' and ''trans'', which differ in the geometry about the central double bond. Nerolidol is present in ], ], ], ], ] and ]. The aroma of nerolidol is woody and reminiscent of fresh bark. It is used as a flavoring agent and in perfumery. It is also currently under testing as a skin penetration enhancer for the ] delivery of therapeutic drugs.<ref>K. Moser et al. European Journal of Pharmaceutics and Biopharmaceutics 52 (2001) 103-112 doi:10.1016/S0939-6411(01)00166-7</ref> |
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'''Nerolidol''', also known as '''peruviol''' and '''penetrol''' , is a naturally occurring ] alcohol. A colorless liquid, it is found in the ]s of many types of plants and flowers.<ref name="Merck"/> There are four ]s of nerolidol', which differ in the geometry about the central double bond and configuration of the hydroxyl-bearing carbon, but most applications use such a mixture. The aroma of nerolidol is woody and reminiscent of fresh bark. It is used as a flavoring agent and in perfumery as well as in non-cosmetic products such as detergents and cleansers.<ref name=":0">{{Cite journal|last1=Chan|first1=Weng-Keong|last2=Tan|first2=Loh Teng-Hern|last3=Chan|first3=Kok-Gan|last4=Lee|first4=Learn-Han|last5=Goh|first5=Bey-Hing|date=2016-04-28|title=Nerolidol: A Sesquiterpene Alcohol with Multi-Faceted Pharmacological and Biological Activities|journal=Molecules|language=en|volume=21|issue=5|pages=529|doi=10.3390/molecules21050529|pmid=27136520|pmc=6272852|doi-access=free}}</ref> '''Nerolidyl''' derivatives include '''nerolidyl''' diphosphate<ref>{{cite journal |last1=Benedict |first1=C. R. |title=The Cyclization of Farnesyl Diphosphate and Nerolidyl Diphosphate by a Purified Recombinant delta-Cadinene Synthase |journal=Plant Physiology |date=1 April 2001 |volume=125 |issue=4 |pages=1754–1765 |doi=10.1104/pp.125.4.1754 |pmid=11299356|pmc=88832 }}{{open access}}</ref> and the fragrance nerolidyl acetate.<ref name=KO/> |
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==Synthesis and occurrence== |
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Nerolidol is produced commercially from ], e.g., by the addition of ] ]. It is used as a source of ], ], and ].<ref name=KO>{{cite book |doi=10.1002/0471238961.2005181602120504.a01.pub2|chapter=Terpenoids |title=Kirk-Othmer Encyclopedia of Chemical Technology |year=2006 |last1=Sell |first1=Charles S. |isbn=0471238961 }}</ref> |
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].]] |
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Significant sources of natural nerolidol is ] oil and the oil of ''Dalbergia parviflora''.<ref name=KO/> It is also present in ], ], ], ], ], '']'', and ], and is a dominant scent compound in '']''.<ref>{{cite book|last1=Kaiser|first1=Roman|title=The Scent of Orchids|date=1993|publisher=Elsevier|isbn=978-0-444-89841-8|pages=58, 199–200}}</ref> |
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==See also== |
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