{{chembox | Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 354914448 | Reference =<ref name="Merck">''Merck Index'', 11th Edition, '''6388'''.</ref> | Name = ''trans''-Nerolidol <small>(top)</small> and ''cis''-Nerolidol <small>(bottom)</small> | ImageFile1 = Nerolidol.png | ImageSize1 = | ImageName1 = ''trans''-Nerolidol | ImageFile2 = Nerolidol - cis.png | ImageSize2 = | ImageName2 = ''cis''-Nerolidol | IUPACName = 3,7,11-Trimethyl-1,6,10-dodecatrien-3-ol | OtherNames = Peruviol |Section1={{Chembox Identifiers | CASNo_Ref = {{cascite|correct|CAS}} | CASNo = 7212-44-4 | CASNo_Comment = (unspecified) | CASNo1_Ref = {{cascite|correct|CAS}} | CASNo1 = 3790-78-1 | CASNo1_Comment = (6-''Z'') | CASNo2_Ref = {{cascite|correct|CAS}} | CASNo2 = 40716-66-3 | CASNo2_Comment = (6-''E'') | UNII_Ref = {{fdacite|correct|FDA}} | UNII = QR6IP857S6 | UNII_Comment = (unspecified) | UNII1_Ref = {{fdacite|correct|FDA}} | UNII1 = 81K23DEF7B | UNII1_Comment = (''cis'') | UNII2_Ref = {{fdacite|correct|FDA}} | UNII2 = FG5V0N8P2H | UNII2_Comment = (''trans'') | PubChem = 8888 | PubChem_Comment = (unspecified) | PubChem1 = 5320128 | PubChem1_Comment = (''cis'') | PubChem2 = 5284507 | PubChem2_Comment = (''trans'') | ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} | ChemSpiderID = 8549 | ChemSpiderID_Comment = (unspecified) | ChemSpiderID1_Ref = {{chemspidercite|changed|chemspider}} | ChemSpiderID1 = 4478283 | ChemSpiderID1_Comment = (''cis'') | ChemSpiderID2_Ref = {{chemspidercite|changed|chemspider}} | ChemSpiderID2 = 4447568 | ChemSpiderID2_Comment = (''trans'') | ChEBI = 7524 | ChEBI_Comment = (unspecified) | ChEBI1 = 173119 | ChEBI1_Comment = (''cis'') | ChEBI2 = 141283 | ChEBI2_Comment = (''trans'') | SMILES = OC(\C=C)(CCC=C(CC/C=C(\C)C)C)C | SMILES_Comment = (unspecified) | SMILES1 = OC(\C=C)(CC\C=C(/CC/C=C(\C)C)C)C | SMILES1_Comment = (''cis'') | SMILES2 = CC(=CCC/C(=C/CCC(C)(C=C)O)/C)C | SMILES2_Comment = (''trans'') | 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 | InChI_Comment = (unspecified) | InChIKey = FQTLCLSUCSAZDY-UHFFFAOYSA-N | 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- | InChI1_Comment = (''cis'') | InChIKey1 = FQTLCLSUCSAZDY-KAMYIIQDSA-N | 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+ | InChI2_Comment = (''trans'') | InChIKey2 = FQTLCLSUCSAZDY-SDNWHVSQSA-N }} |Section2={{Chembox Properties |RefractIndex= 1.4898 | Formula = C<sub>15</sub>H<sub>26</sub>O | MolarMass = 222.37 g/mol | Density = 0.872 g/cm<sup>3</sup> | MeltingPt = | BoilingPtC = 122 | BoilingPt_notes = at 3 mmHg }} }}
'''Nerolidol''', also known as '''peruviol''' and '''penetrol''', is a naturally occurring sesquiterpene alcohol. A colorless liquid, it is found in the essential oils of many types of plants and flowers.<ref name="Merck"/> There are four isomers 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> It has pronounced pharmacological properties: antimicrobial, antiparasitic, anti-inflammatory<ref>{{Cite web |title=Неролидол (C₁₅H₂₆O): химические свойства, природные источники и применение |url=https://nerolidol.ru/ |access-date=2026-04-09 |website=nerolidol.ru}}</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/>
==Synthesis and occurrence== Nerolidol is produced commercially from geranylacetone, e.g., by the addition of vinyl Grignard reagent. It is used as a source of farnesol, vitamin E, and vitamin K1.<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> [[File:GeranylacetoneToFarnesolviaNerolidol.svg|thumb|840px|center|Conversion of geranylacetone to nerolidol, which can be isomerized to farnesol.]]
Significant sources of natural nerolidol is Cabreuva oil and the oil of ''Dalbergia parviflora''.<ref name=KO/> It is also present in neroli, ginger, jasmine, lavender, tea tree, ''Cannabis sativa'', and lemon grass, and is a dominant scent compound in ''Brassavola nodosa''.<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>
==See also== * Linalool * Farnesol * Geranylfarnesol
==References== {{reflist}}
Category:Tertiary alcohols Category:Perfume ingredients Category:Flavors Category:Sesquiterpenes