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Revision as of 14:50, 21 January 2011 editCheMoBot (talk | contribs)Bots141,565 edits Updating {{chembox}} (no changed fields - added verified revid - updated 'UNII_Ref', 'ChEMBL_Ref', 'KEGG_Ref') per Chem/Drugbox validation (report errors← Previous edit Latest revision as of 14:58, 8 June 2023 edit undoCitation bot (talk | contribs)Bots5,433,932 edits Add: bibcode. | Use this bot. Report bugs. | Suggested by Spinixster | Category:Isopropyl compounds | #UCB_Category 10/169 
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{{chembox {{chembox
| Watchedfields = changed
| verifiedrevid = 409170782 | verifiedrevid = 464385786
| Reference=<ref>'']''. 5, '''IV''', 451</ref> | Reference =<ref>'']''. 5, '''IV''', 451</ref>
⚫ | Name = Sabinene
| ImageFile = Sabinene.png | Name = Sabinene
| ImageFile = (±)-Sabinene Structural Formulea V.1.svg
| ImageSize = 120px | ImageSize = 290px
| ImageName = Sabinene
⚫ | ImageName = Sabinene
| IUPACName = 4-methylene-1-(1-methylethyl)bicyclohexane | IUPACName = 4-methylene-1-(1-methylethyl)bicyclohexane
| Section1 = {{Chembox Identifiers |Section1={{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 17769 | ChemSpiderID = 17769
| PubChem = 18818 | PubChem = 18818
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| StdInChIKey = NDVASEGYNIMXJL-UHFFFAOYSA-N | StdInChIKey = NDVASEGYNIMXJL-UHFFFAOYSA-N
| CASNo_Ref = {{cascite|correct|CAS}} | CASNo_Ref = {{cascite|correct|CAS}}
| CASNo=3387-41-5 | CASNo = 3387-41-5
| CASNo1_Ref = {{cascite|correct|CAS}}
| CASOther = (±)<br /> (+) <br /> (-)
| CASNo1 = 10408-16-9
⚫ | SMILES = C=C2C1CC1(C(C)C)CC2
| CASNo1_Comment = (-)
| CASNo2 = 2009-00-9
| CASNo2_Ref = {{cascite|correct|CAS}}
| CASNo2_Comment = (+)

| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 7D1TL44GPC
| UNII1_Ref = {{fdacite|correct|FDA}}
| UNII1 = I223NX31W9
| UNII1_Comment = (-)
| UNII2_Ref = {{fdacite|correct|FDA}}
| UNII2 = XYL0G8758O
| UNII2_Comment = (+)

| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 50027
⚫ | SMILES = C=C2C1CC1(C(C)C)CC2
}} }}
| Section2 = {{Chembox Properties |Section2={{Chembox Properties
| Formula = C<sub>10</sub>H<sub>16</sub> | Formula = C<sub>10</sub>H<sub>16</sub>
| MolarMass = 136.23 g/mol | MolarMass = 136.23 g/mol
| Density = 0.844 g/mL at 20 °C g/cm<sup>3</sup> | Density = 0.844 g/mL at 20 °C g/cm<sup>3</sup>
| MeltingPt = | MeltingPt =
| BoilingPt = 163-164 °C | BoilingPtC = 163 to 164
| BoilingPt_notes =
}} }}
}} }}


'''Sabinene''' is a natural bicyclic ] with the molecular formula C<sub>10</sub>H<sub>16</sub>. It is isolated from the ]s of a variety of plants including ] (''Quercus ilex'') and ] (''Picea abies''). It has a strained ring system with ] ring fused to a ] ring. '''Sabinene''' is a natural bicyclic ] with the molecular formula C<sub>10</sub>H<sub>16</sub>. It is isolated from the ]s of a variety of plants including ],<ref>{{Cite journal|url=http://www.tandfonline.com/doi/abs/10.1080/0972060X.2014.935039|doi=10.1080/0972060X.2014.935039|title=Changes in the Essential Oil Composition of ''Origanum'' majoranaL. During Post Harvest Drying|year=2016|last1=Verma|first1=Ram S.|last2=Padalia|first2=Rajendra C.|last3=Chauhan|first3=Amit|last4=Verma|first4=Rajesh K.|last5=Ur Rahman|first5=Laiq|last6=Singh|first6=Anand|journal=Journal of Essential Oil Bearing Plants|volume=19|issue=6|pages=1547–1552|s2cid=99578528}}</ref> ] (''Quercus ilex'') and ] (''Picea abies''). It has a strained ring system with a ] ring fused to a ] ring.


Sabinene is one of the chemical compounds that contributes to the spiciness of ] and is a major constituent of carrot seed oil. It also occurs in tea tree oil at a low concentration.It is also present in the essential oil obtained from nutmeg. Sabinene is one of the chemical compounds that contributes to the spiciness of ] and is a major constituent of ]. It also occurs in tea tree oil at a low concentration. It is also present in the essential oil obtained from nutmeg,<ref>{{Cite journal
| last1 = Shulgin | first1 = A. T.
| last2 = Sargent | first2 = T.
| last3 = Naranjo | first3 = C.
| title = The Chemistry and Psychopharmacology of Nutmeg and of Several Related Phenylisopropylamines
| journal = Psychopharmacology Bulletin
| volume = 4
| issue = 3
| pages = 13
| year = 1967
| pmid = 5615546
| url = http://bitnest.ca/external.php?id=%250E%253D9%250F%2524G%252F%2518B%255B%255B4%2522.FXQ%255CO%2500TK
| format = pdf
}}</ref> '']'', and '']''.

== Biosynthesis ==
Sabinene, a bicyclic monoterpene, is present in the (+) and (-) ]s.<ref name=":0">{{Cite journal|last1=Cao|first1=Yujin|last2=Zhang|first2=Haibo|last3=Liu|first3=Hui|last4=Liu|first4=Wei|last5=Zhang|first5=Rubing|last6=Xian|first6=Mo|last7=Liu|first7=Huizhou|date=2018-02-01|title=Biosynthesis and production of sabinene: current state and perspectives|url=https://doi.org/10.1007/s00253-017-8695-5|journal=Applied Microbiology and Biotechnology|language=en|volume=102|issue=4|pages=1535–1544|doi=10.1007/s00253-017-8695-5|pmid=29264773|s2cid=27685411|issn=1432-0614}}</ref> It is biosynthesized from the common terpenoid precursor, ] (GPP) that undergoes polycyclization catalyzed by sabinene synthase (SabS).<ref name=":0" /><ref>{{Cite journal|last1=Peters|first1=R.J.|last2=Croteau|first2=R. B.|date=2003-09-15|title=Alternative termination chemistries utilized by monoterpene cyclases: chimeric analysis of bornyl diphosphate, 1,8-cineole, and sabinene synthases|url=https://www.sciencedirect.com/science/article/abs/pii/S0003986103003473|journal=Archives of Biochemistry and Biophysics|language=en|volume=417|issue=2|pages=203–211|doi=10.1016/S0003-9861(03)00347-3|pmid=12941302|issn=0003-9861}}</ref> GPP is formed from the terpenoid synthesis pathway with the starter units, ] (IPP) and ] (DMAPP). The starter units, IPP and DMAPP, can be synthesized from either the ] or the ].<ref name=":0" /> With the head-to-tail condensation of IPP and DMAPP catalyzed by GPP synthase, GPP is formed. Sabinene synthase (SabS) then catalyzes the ionization and isomerization of GPP to form 3R-linalyl pyrophosphate.<ref name=":0" /><ref name=":1">{{Cite journal|last1=Adam|first1=K. P.|last2=Croteau|first2=R.|date=1998-09-28|title=Monoterpene Biosynthesis in the Liverwort Conocephalum Conicum: Demonstration of Sabinene Synthase and Bornyl Diphosphate Synthase in Honour of Professor G. H. Neil Towers 75th Birthday|url=https://www.sciencedirect.com/science/article/abs/pii/S0031942297007413|journal=Phytochemistry|language=en|volume=49|issue=2|pages=475–480|doi=10.1016/S0031-9422(97)00741-3|pmid=9747540|bibcode=1998PChem..49..475A |issn=0031-9422}}</ref> Further ionization and cyclization results in the formation of sabinene.

]


==See also== ==See also==
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