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Revision as of 13:23, 10 January 2012 editThe chemistds (talk | contribs)Extended confirmed users5,761 edits added/refreshed (Std)InChI and (Std)InChIKey← Previous edit		Latest revision as of 19:00, 10 November 2024 edit undoSmokefoot (talk | contribs)Autopatrolled, Extended confirmed users, Pending changes reviewers, Rollbackers75,107 edits rose alcohols
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			{{Short description|Chemical compound with a floral aroma}}
	{{chembox		{{chembox
	| Verifiedfields = changed		| Verifiedfields = changed
	| Watchedfields = changed		| Watchedfields = changed
	| verifiedrevid = 416801762		| verifiedrevid = 470609278
	| ImageFile = Linalool-skeletal.png		| ImageFile = Linalool skeletal.svg
	| ImageSize =		| ImageSize = 240
			| ImageAlt = Skeletal formula
	| IUPACName = 3,7-dimethylocta-1,6-dien-3-ol
			| ImageFile1 = (S)-Linalool molecule ball.png
	| Section1 = {{Chembox Identifiers
	| CASNo = 78-70-6		| ImageSize1 = 240
			| ImageAlt1 = Ball-and-stick model
	| CASNo_Ref = {{cascite|correct|CAS}}
			| PIN = 3,7-Dimethylocta-1,6-dien-3-ol
	| PubChem = 6549
			| OtherNames = 3,7-Dimethyl-1,6-octadien-3-ol, β-linalool, linalyl alcohol, linaloyl oxide, allo-ocimenol, coriandrol, Licareol
	| ChEMBL_Ref = {{ebicite|changed|EBI}}
			|Section1={{Chembox Identifiers
	| ChEMBL = 25306
			| index_label =
	| UNII_Ref = {{fdacite|changed|FDA}}
			| index1_label = (''R'')
			| index2_label = (''S'')
			| index_comment = (±)-linalool
			| index1_comment = (−)-linalool
			| index2_comment = (+)-linalool
			| testQID = Q410932
			| QID1 = Q27105200
			| QID2 = Q27105233
			| IUPHAR_ligand = 2469
			| CASNo = 78-70-6
			| CASNo_Ref = {{cascite|correct|CAS}}
			| CASNo1 = 126-91-0
			| CASNo1_Ref = {{cascite|correct|CAS}}
			| CASNo2 = 126-90-9
			| CASNo2_Ref = {{cascite|correct|CAS}}
			| PubChem = 6549
			| PubChem1 = 443158
			| PubChem2 = 67179
			| ChEMBL_Ref = {{ebicite|correct|EBI}}
			| ChEMBL = 25306
			| ChEMBL2 = 235672
			| KEGG1 = C11388
			| KEGG2 = C11389
			| 3DMet = B05103
			| UNII_Ref = {{fdacite|correct|FDA}}
	| UNII = D81QY6I88E		| UNII = D81QY6I88E
			| UNII1_Ref = {{fdacite|correct|FDA}}
			| UNII1 = 3U21E3V8I2
			| UNII2_Ref = {{fdacite|correct|FDA}}
			| UNII2 = F4VNO44C09
			| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
	| ChemSpiderID = 13849981		| ChemSpiderID = 13849981
	| ChEBI_Ref = {{ebicite|changed|EBI}}		| ChEBI_Ref = {{ebicite|correct|EBI}}
	| ChEBI = 17580		| ChEBI = 17580
			| ChEBI1 = 28
	| InChI = 1/C10H18O/c1-5-10(4,11)8-6-7-9(2)3/h5,7,11H,1,6,8H2,2-4H3
			| ChEBI2 = 98
	| InChIKey = CDOSHBSSFJOMGT-UHFFFAOYAV
	| StdInChI = 1S/C10H18O/c1-5-10(4,11)8-6-7-9(2)3/h5,7,11H,1,6,8H2,2-4H3		| InChI = 1/C10H18O/c1-5-10(4,11)8-6-7-9(2)3/h5,7,11H,1,6,8H2,2-4H3
	| StdInChIKey = CDOSHBSSFJOMGT-UHFFFAOYSA-N		| InChIKey = CDOSHBSSFJOMGT-UHFFFAOYAV
			| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
			| StdInChI = 1S/C10H18O/c1-5-10(4,11)8-6-7-9(2)3/h5,7,11H,1,6,8H2,2-4H3
			| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
			| StdInChIKey = CDOSHBSSFJOMGT-UHFFFAOYSA-N
	| SMILES = CC(O)(C=C)CCC=C(C)C		| SMILES = CC(O)(C=C)CCC=C(C)C
	}}		}}
	| Section2 = {{Chembox Properties		|Section2={{Chembox Properties
			| C=10|H=18|O=1
	| Formula = C<sub>10</sub>H<sub>18</sub>O
			| Appearance = Colorless oil
	| MolarMass = 154.25 g/mol
			| Density = 0.858 to 0.868 g/cm<sup>3</sup>
	| Appearance =
			| MeltingPt= <
	| Density = 0.858 – 0.868 g/cm<sup>3</sup>
	| MeltingPt = < −20&nbsp;°C		| MeltingPtC = −20
			| BoilingPtC = 198 to 199
	| BoilingPt = 198–199&nbsp;°C
			| BoilingPt_notes =
	| Solubility = 1.589 g/l
			| Solubility = 1.589 g/l
	}}
	| Section3 = {{Chembox Hazards
	| MainHazards =
	| FlashPt = 55&nbsp;°C
	| Autoignition =
	}}		}}
			|Section3={{Chembox Hazards
			| NFPA-H = 1
			| NFPA-F = 2
			| NFPA-R = 0
			| MainHazards =
			| FlashPtC = 55
			| AutoignitionPtC =
			}}
	}}		}}
	'''Linalool''' ({{IPAc-en|icon|l|ɪ|ˈ|n|æ|l|ɵ|.|ɒ|l}}) is a naturally occurring ] ] chemical found in many ]s and ] plants with many commercial applications, the majority of which are based on its pleasant scent (floral, with a touch of spiciness). It has other names such as β-linalool, linalyl alcohol, linaloyl oxide, ''p''-linalool, allo-ocimenol, and 2,6-dimethyl-2,7-octadien-6-ol.		'''Linalool''' ({{IPAc-en|l|ᵻ|ˈ|n|æ|l|oʊ|ɒ|l|,_|l|aɪ|-|,_|-|l|oʊ|oʊ|l|,_|-|ˈ|l|uː|l}}) refers to two ]s of a naturally occurring ] ] found in many ]s and ] plants.<ref name="pubchem">{{cite web |title=Linalool |url=https://pubchem.ncbi.nlm.nih.gov/compound/6549 |publisher=PubChem, US National Library of Medicine |access-date=17 October 2021 |date=16 October 2021}}</ref> Together with ], ], ], linalool is one of the '''rose alcohols'''.<ref name=KO/> Linalool has multiple commercial applications, the majority of which are based on its pleasant scent (floral, with a touch of spiciness).<ref name="Ullmann">{{Ullmann |doi=10.1002/14356007.a26_205|title=Terpenes|year= 2000|last1=Eggersdorfer|first1=Manfred}}</ref><ref>{{cite journal |doi=10.1016/S0278-6915(03)00015-2|title=Fragrance material review on linalool|year=2003|last1=Letizia|first1=C.S|last2=Cocchiara|first2=J.|last3=Lalko|first3=J.|last4=Api|first4=A.M|journal=Food and Chemical Toxicology|volume=41|issue=7|pages=943–964|pmid=12804650}}</ref>
			A colorless oil, linalool is classified as an acyclic ].<ref name=pubchem/> In plants, it is a ], a ] component, an ] agent, and an ].<ref name=pubchem/> Linalool has uses in manufacturing of soaps, fragrances, ]s as flavors, household products, and ]s.<ref name=pubchem/> ]s of linalool are referred to as '''linalyl''', e.g. linalyl ], an isomer of ].<ref name=Crot>{{cite journal |pmid=3392006|year=1988|last1=Croteau|first1=R.|last2=Satterwhite|first2=D. M.|last3=Cane|first3=D. E.|last4=Chang|first4=C. C.|title=Biosynthesis of Monoterpenes. Enantioselectivity in the Enzymatic Cyclization of (+)- and (-)-Linalyl Pyrophosphate to (+)- and (-)-Pinene and (+)- and (-)-Camphene|journal=The Journal of Biological Chemistry|volume=263|issue=21|pages=10063–71|doi=10.1016/S0021-9258(19)81477-1 |doi-access=free }}</ref>
	==In nature==
			The word ''linalool'' is based on '']'' (a type of wood) and the suffix ''{{linktext|-ol}}''.<ref>{{Merriam-Webster|Linalool}}: "International Scientific Vocabulary, from Mexican Spanish lináloe"</ref> In food manufacturing, it may be called ''coriandrol''.<ref name=pubchem/>
	Over 200 species of plants produce linalool, mainly from the families ] (mints, scented herbs), ] (laurels, cinnamon, rosewood), and ] (citrus fruits), but also birch trees and other plants, from tropical to boreal climate zones. It has also been found in some fungi.
	==Enantiomers==		==Occurrence==
			]
	Linalool has a stereogenic center at C<sub>3</sub> and therefore two stereoisomers: '''licareol''' is (''R'')-(–)-linalool with CAS No. 126–90–9 (PubChem 67179) and '''coriandrol''' is (''S'')-(+)-linalool with CAS No. 126–91–0 (PubChem 13562).
			Both ]ic forms are found in nature: (''S'')-linalool is found, for example, as a major constituent of the essential oils of ] ('']'' L.), ] ('']'' var. ''martinii''), and ] ('']'') flowers. (''R'')-linalool is present in ] ('']''), ] (''Laurus nobilis''), and ] (''Ocimum basilicum''), among others.
			Each enantiomer evokes distinct neural responses in humans, so each is classified as possessing distinct ]s. (''S'')-(+)-Linalool is perceived as sweet, floral, ]-like (odor threshold 7.4&nbsp;]) and the (''R'')-form as more woody and ]-like (odor threshold 0.8&nbsp;]).
	]
			Over 200 species of plants produce linalool, notably from the families ] (] and other herbs), ] (], ], ]), and ] (]), but also ] and other plants, from ] to ] zones.
	Both enantiomeric forms are found in nature: S-linalool is found, for example, as a major constituent of the essential oils of ] (''Coriandrum sativum'' L. family ]) seed, ] ]], and ] (''Citrus sinensis'' Osbeck, family ]) flowers. (R)-linalool is present in ] (''Lavandula officinalis'' Chaix, family ]), ] (''Laurus nobilis'', family ]), and ] (''Ocimum basilicum'', family ]), among others.
			* '']''
	Each enantiomer evokes different neural responses in humans, and therefore are classified as possessing distinct scents. 3S-(+)-linalool is perceived as sweet, floral, petitgrain-like (odor threshold 7.4 ppb) and the 3R-form as more woody and ]-like (odor threshold 0.8 ppb)
			* '']''<ref>{{cite journal | vauthors = Kasper S, Gastpar M, Müller WE, Volz HP, Möller HJ, Dienel A, Schläfke S | title = Silexan, an orally administered Lavandula oil preparation, is effective in the treatment of 'subsyndromal' anxiety disorder: a randomized, double-blind, placebo controlled trial | journal = International Clinical Psychopharmacology | volume = 25 | issue = 5 | pages = 277–87 | date = September 2010 | pmid = 20512042 | doi = 10.1097/YIC.0b013e32833b3242 | s2cid = 46290020 }}</ref>
			* '']''<ref name=eocs>{{cite journal | vauthors = Ahmed A, Choudhary MI, Farooq A, Demirci B, Demirci F, Can Başer KH | title = Essential oil constituents of the spice ''Cinnamomum tamala'' (Ham.) Nees & Eberm. | journal = Flavour and Fragrance Journal | volume = 15 | issue = 6 | pages = 388–390 | year = 2000 | doi = 10.1002/1099-1026(200011/12)15:6<388::AID-FFJ928>3.0.CO;2-F | doi-access = free }}</ref>
			* '']''<ref name="Ibrahim">{{cite journal | vauthors = Ibrahim EA, Wang M, Radwan MM, Wanas AS, Majumdar CG, Avula B, Wang YH, Khan IA, Chandra S, Lata H, Hadad GM, Abdel Salam RA, Ibrahim AK, Ahmed SA, ElSohly MA | display-authors = 6 | title = Analysis of Terpenes in Cannabis sativa L. Using GC/MS: Method Development, Validation, and Application | journal = Planta Medica | volume = 85 | issue = 5 | pages = 431–438 | date = March 2019 | pmid = 30646402 | doi = 10.1055/a-0828-8387 | s2cid = 58668648 }}</ref>
			* '']''<ref name=apfb>{{cite journal | vauthors = Klimankova E, Holadová K, Hajšlová J, Čajka T, Poustka J, Koudela M | title = Aroma profiles of five basil (''Ocimum basilicum'' L.) cultivars grown under conventional and organic conditions | journal = Food Chemistry | volume = 107 | issue = 1 | pages = 464–472 | year = 2008 | doi = 10.1016/j.foodchem.2007.07.062 }}</ref>
			* '']'' (goldenrod)<ref>{{cite journal | vauthors = Vila R, Mundina M, Tomi F, Furlán R, Zacchino S, Casanova J, Cañigueral S | title = Composition and antifungal activity of the essential oil of Solidago chilensis | journal = Planta Medica | volume = 68 | issue = 2 | pages = 164–7 | date = February 2002 | pmid = 11859470 | doi = 10.1055/s-2002-20253 | s2cid = 260283973 }}</ref>
			* '']'' (mugwort)
			* '']'' (hop)
			It was first synthesized in the laboratory of ] in 1919.<ref name=em90>Albert Eschenmoser: "Leopold Ruzicka - From the Isoprene Rule to the Question of Life's Origin" CHIMIA 44 (1990)</ref>
	==Biosynthesis==
	In higher plants linalool, as other monoterpenoids, is produced from isopentenyl pyrophosphate via the universal isoprenoid intermediate geranyl pyrophosphate, through a class of membrane-bound enzymes named monoterpene synthases. One of these, linalool synthase (LIS), has been reported to produce (S)-linalool in several floral tissues.
	==Uses==		==Production==
			Linalool is produced commercially from several terpenes and terpenoid precursors, which are often components of ]. 2-Pinanol, derived from ], gives ] upon pyrolysis.<ref>{{Ullmann |doi=10.1002/14356007.a26_205|title=Terpenes |year=2000 |last1=Eggersdorfer |first1=Manfred |isbn=3527306730 }}</ref>
	Linalool is used as a scent in 60–80% of perfumed hygiene products and cleaning agents including soaps, detergents, shampoos, and lotions.<ref name="MedicalNewsToday">{{Cite news |url=http://www.medicalnewstoday.com/articles/144041.php |title=Widely Used Fragrance Ingredients In Shampoos And Conditioners Are Frequent Causes Of Eczema &#124;date March 28 2009}}</ref> It is also used as a ]. One common downstream product of linalool is ]. In addition, linalool is used by pest professionals as a flea and cockroach insecticide.
			===Biosynthesis===
	Linalool is used in some mosquito repellent products, however the EPA notes that: "A preliminary screen of labels for products containing Linalool (as the sole active ingredient) indicates that efficacy data on file with the Agency may not support certain claims to repel mosquitos."<ref name="EPA"></ref>
			In ] linalool is formed by rearrangement of ] (GPP).<ref name="Planta Medica">{{cite journal | vauthors = Woronuk G, Demissie Z, Rheault M, Mahmoud S | title = Biosynthesis and therapeutic properties of Lavandula essential oil constituents | journal = Planta Medica | volume = 77 | issue = 1 | pages = 7–15 | date = January 2011 | pmid = 20665367 | doi = 10.1055/s-0030-1250136 | doi-access = free }}</ref> With the aid of ] (LIS), water attacks to form the chiral center.<ref>{{cite book |last1=Dewick |first1=Paul M | name-list-style = vanc |title=Medicinal Natural Products: A Biosynthetic Approach |date=2009 |publisher=John Wiley & Sons |isbn=978-0-470-74168-9 |edition=3rd}}</ref><ref name="Planta Medica"/> LIS appears to show a ]-type catalysis through a simplified "metal-cofactor-binding domain of the residues involved in substrate...binding in the C-terminal part of the protein" suggesting ] and the reasoning behind why some plants have varying levels of each enantiomer.<ref name="Molecular Biology and Evolution">{{cite journal | vauthors = Cseke L, Dudareva N, Pichersky E | title = Structure and evolution of linalool synthase | journal = Molecular Biology and Evolution | volume = 15 | issue = 11 | pages = 1491–8 | date = November 1998 | pmid = 12572612 | doi = 10.1093/oxfordjournals.molbev.a025876 | doi-access = free }}</ref><ref name="Plant Physiol">{{cite journal | vauthors = Iijima Y, Davidovich-Rikanati R, Fridman E, Gang DR, Bar E, Lewinsohn E, Pichersky E | title = The biochemical and molecular basis for the divergent patterns in the biosynthesis of terpenes and phenylpropenes in the peltate glands of three cultivars of basil | journal = Plant Physiology | volume = 136 | issue = 3 | pages = 3724–36 | date = November 2004 | pmid = 15516500 | pmc = 527170 | doi = 10.1104/pp.104.051318 | doi-access = free }}</ref>
			] ]. Abbreviations used: geranyl diphosphate synthase (GDS), pyrophosphate ester (OPP), ] (IPP), ] (DMAPP), geranyl pyrophosphate (GPP). Stereogenic centers are indicated by an asterisk.|654x654px]]
			==Odor and flavor==
	Akio Nakamura together with colleagues from the University of Tokyo and T. Hasegawa Co., Ltd in Kawasaki, Japan, claim to have demonstrated that inhaling linalool can reduce stress in lab rats. In a study published in The Journal of Agriculture and Food Chemistry,<ref name=jafc>{{cite journal
			Linalool has complex odor and flavor properties. Its odor is similar to floral, spicy wood, somewhat resembling ] plants, ] or ].<ref name=pubchem/> It has a light, citrus-like flavor, sweet with a spicy tropical accent.<ref name=pubchem/> Linalool is used as a scent in ]d hygiene products and cleaning agents, including ]s, ]s, ]s, and lotions.<ref name=pubchem/><ref name="Ullmann"/> It exhibits antimicrobial and antifungal properties.<ref name=pubchem/><ref>{{cite journal |doi=10.1016/j.foodchem.2007.12.010|title=Chemical composition, antioxidant and antimicrobial activities of basil (Ocimum basilicum) essential oils depends on seasonal variations|year=2008|last1=Hussain|first1=Abdullah Ijaz|last2=Anwar|first2=Farooq|last3=Hussain Sherazi|first3=Syed Tufail|last4=Przybylski|first4=Roman|journal=Food Chemistry|volume=108|issue=3|pages=986–995|pmid=26065762}}</ref>
	| last = Nakamura
	| first = Akio ''et al.''
	| title = Stress Repression in Restrained Rats by (R)-(−)-Linalool Inhalation and Gene Expression Profiling of Their Whole Blood Cells
	| journal = The Journal of Agriculture and Food Chemistry
	| volume = 57
	| issue = 12
	| pages = 5480–5485
	| publisher = American Chemical Society
	| date = 20 May 2009
	| url = http://pubs.acs.org/doi/abs/10.1021/jf900420g
	| doi = 10.1021/jf900420g
	| accessdate = 22 January 2010
	| pmid = 19456160
	| last2 = Fujiwara
	| first2 = S
	| last3 = Matsumoto
	| first3 = I
	| last4 = Abe
	| first4 = K}}</ref> they exposed the animals to stressful conditions and found that those inhaling linalool saw their stress-elevated levels of neutrophils and lymphocytes fall to near-normal levels compared with the controls. Inhaling linalool also reduced the activity of more than 100 genes that "go into overdrive" in stressful situations. The findings could form the basis of new blood tests for identifying fragrances that can soothe stress, the researchers claim.<ref name="ScienceDaily">{{Cite news |url=http://www.sciencedaily.com/releases/2009/07/090722110901.htm |title=Stop and Smell the Flowers -- The Scent Can Really Soothe Stress |date=July 22, 2009}}<!-- paper article is referencing: <ref name=jafc> --></ref>
			==Chemical derivatives==
	==List of the plants that contain the chemical==
			Linalool is hydrogenated to give dihydro- and tetrahydrolinalool, which are fragrances that are more resilient toward oxidants, as might be found in household cleaning products. ], a popular scent, is produced by esterification of linalool (as well as occurring naturally). Isomerization of linalool gives ] 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>
	* ]<ref name=eocs>{{cite journal
	| last = Ahmed
	| first = Aftab ''et al.''
	| title = Essential oil constituents of the spice ''Cinnamomum tamala'' (Ham.) Nees & Eberm
	| journal = Flavour and Fragrance Journal
	| volume = 15
	| issue = 6
	| pages = 388–390
	| year = 2000
	| doi = 10.1002/1099-1026(200011/12)15:6<388::AID-FFJ928>3.0.CO;2-F
	| last2 = Choudhary
	| first2 = M. Iqbal
	| last3 = Farooq
	| first3 = Afgan
	| last4 = Demirci
	| first4 = Betül
	| last5 = Demirci
	| first5 = Fatih
	| last6 = Can Başer
	| first6 = K. Hüsnü}}</ref>{{Clarify|date=July 2009}}
	* ]<ref name=apfb>{{cite journal
	| last = Klimánková
	| first = Eva ''et al.''
	| title = Aroma profiles of five basil (Ocimum basilicum L.) cultivars grown under conventional and organic conditions
	| journal = Food Chemistry
	| volume = 107
	| issue = 1
	| pages = 464–472
	| year = 2008
	| doi = 10.1016/j.foodchem.2007.07.062
	| last2 = Holadová
	| first2 = Kateřina
	| last3 = Hajšlová
	| first3 = Jana
	| last4 = Čajka
	| first4 = Tomáš
	| last5 = Poustka
	| first5 = Jan
	| last6 = Koudela
	| first6 = Martin}}</ref>{{Clarify|date=July 2009}}
	* '']'' Meyen<ref>{{Cite journal
	| last1 = Vila | first1 = R.
	| last2 = Mundina | first2 = M.
	| last3 = Tomi | first3 = F. L.
	| last4 = Furlán | first4 = R.
	| last5 = Zacchino | first5 = S.
	| last6 = Casanova | first6 = J.
	| last7 = Cañigueral | first7 = S.
	| doi = 10.1055/s-2002-20253
	| title = Composition and Antifungal Activity of the Essential Oil of Solidago chilensis
	| journal = Planta Medica
	| volume = 68
	| issue = 2
	| pages = 164–167
	| year = 2002
	| pmid = 11859470
	}}</ref>
	* ], also known as mugwort
	==Safety information==		==Safety==
			Linalool can be absorbed by inhalation of its ] and by oral intake or skin absorption, potentially causing irritation, pain and ] reactions.<ref name="Ullmann" /><ref>{{cite web |title=Linalool |url=https://toxnet.nlm.nih.gov/cgi-bin/sis/search/a?dbs+hsdb:@term+@DOCNO+645 | archive-url = https://web.archive.org/web/20190228004550/https://toxnet.nlm.nih.gov/cgi-bin/sis/search/a?dbs+hsdb:@term+@DOCNO+645 | archive-date = 28 February 2019 |publisher=Toxnet, National Library of Medicine, US National Institutes of Health |access-date=21 May 2019 |date=14 January 2016}}</ref> Some 7% of people undergoing ]ing in Europe were found to be allergic to the ] of linalool.<ref>{{cite journal | vauthors = Ung CY, White JM, White IR, Banerjee P, McFadden JP | title = Patch testing with the European baseline series fragrance markers: a 2016 update | journal = The British Journal of Dermatology | volume = 178 | issue = 3 | pages = 776–780 | date = March 2018 | pmid = 28960261 | doi = 10.1111/bjd.15949 | s2cid = 4434234 }}</ref>
	Linalool gradually breaks down when in contact with oxygen, forming an oxidized by-product that may cause allergic reactions such as eczema in susceptible individuals. Between 5–7% of patients undergoing patch testing in Sweden were found to be allergic to the oxidized form of linalool.<ref name="MedicalNewsToday"/> Ways to minimize exposure include not buying large bottles of perfumed hygiene products, and replacing the lid after each use.
			The US Food and Drug Administration (FDA) lists linalool in the Code of Federal Regulations under substances generally recognized as safe, synthetic flavoring substances and adjuvants.<ref name="21CFR182.60">{{cite web | title=eCFR :: 21 CFR 182.60 -- Synthetic flavoring substances and adjuvants. | website=eCFR | date=2021-10-27 | url=https://www.ecfr.gov/current/title-21/chapter-I/subchapter-B/part-182/subpart-A/section-182.60 | access-date=2021-10-29}}</ref>
	==Notes and references==
	===Notes===
	<references />
	===General references===
	* Casabianca H, Graff JB, Faugier V, Fleig F, Grenier C (1998) Enantiomeric distribution studies of linalool and linalyl acetate. A powerful tool for authenticity control of essential oils. HRC J High Res Chrom 21:107-112
			== See also ==
	* Lewinshon E, Schalechet F, Wilkinson J, Matsui K, Tadmor Y, Nam K, Amar O, Lastochkin E, Larkov O, Ravid U, Hiatt W, Gepstein S, Pichersky E (2001) Enhanced levels of the aroma and flavor compound S-linalool by metabolic engineering of the terpenoid pathway in tomato fruits. Plant Physiol 127:1256–1265
			* ]
			== References ==
	* Pengelly, Andrew. The Constituents of Medicinal Plants. 2nd Ed. 2004. CABI Publishing, U.S.A. and UK.
			{{reflist}}
			== External links ==
	* Raguso RA, Pichersky E (1999) A day in the life of a linalool molecule: chemical communication in a plant-pollinator system. Part 1: linalool biosynthesis in flowering plants. Plant Species Biol 14:95-120
			*
			* {{CPID|id=2771}}
			{{Transient receptor potential channel modulators}}
	* Akio Nakamura, Satoshi Fujiwara, Ichiro Matsumoto and Keiko Abe. Stress Repression in Restrained Rats by (R)-(−)-Linalool Inhalation and Gene Expression Profiling of Their Whole Blood Cells. J. Agric. Food Chem., 2009, 57 (12), pp 5480–5485.
	==See also==
	* ]
	* ]
	==External links==
	*
	* {{HPD|2771}}
	]		]
	]		]
	]		]
	]		]
	]		]
			]
	]
	]
	]
	]
	]
	]
	]
	]
	]
	]
	]
	]
	]
	]
	]
	]