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Sabinene

Sabinene is a natural bicyclic monoterpene with the molecular formula C10H16. It is isolated from the essential oils of a variety of plants including Marjoram, holm oak (Quercus ilex) and Norway spruce (Picea abies). It has a strained ring system with a cyclopentane ring fused to a cyclopropane ring.

Sabinene
Names
IUPAC name
4-methylene-1-(1-methylethyl)bicyclo[3.1.0]hexane
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.020.194
KEGG
UNII
  • InChI=1S/C10H16/c1-7(2)10-5-4-8(3)9(10)6-10/h7,9H,3-6H2,1-2H3 Y
    Key: NDVASEGYNIMXJL-UHFFFAOYSA-N Y
  • InChI=1/C10H16/c1-7(2)10-5-4-8(3)9(10)6-10/h7,9H,3-6H2,1-2H3
    Key: NDVASEGYNIMXJL-UHFFFAOYAW
  • C=C2C1CC1(C(C)C)CC2
Properties
C10H16
Molar mass 136.23 g/mol
Density 0.844 g/mL at 20 °C g/cm3
Boiling point 163 to 164 °C (325 to 327 °F; 436 to 437 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Yverify (what is YN ?)
Infobox references

Sabinene is one of the chemical compounds that contributes to the spiciness of black pepper 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, Laurus nobilis, and Clausena anisata.

Sabinene, a bicyclic monoterpene, is present in the (+) and (-) enantiomers. It is biosynthesized from the common terpenoid precursor, geranyl pyrophosphate (GPP) that undergoes polycyclization catalyzed by sabinene synthase (SabS). GPP is formed from the terpenoid synthesis pathway with the starter units, isopentenyl pyrophosphate (IPP) and dimethylallyl pyrophosphate (DMAPP). The starter units, IPP and DMAPP, can be synthesized from either the mevalonate (MVA) or the methylerythritol 4-phosphate (MEP) pathway. 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. Further ionization and cyclization results in the formation of sabinene.

With the biosynthesis catalyzed by sabinene synthase, the precursor, geranyl pyrophosphate, undergoes isomerization and cyclization to form sabinene.
  • Thujene, a double bond isomer of sabinene
  1. Beilstein. 5, IV, 451
  2. www.tandfonline.com/doi/abs/10.1080/0972060X.2014.935039
  3. Shulgin, A. T.; Sargent, T.; Naranjo, C. (1967). "The Chemistry and Psychopharmacology of Nutmeg and of Several Related Phenylisopropylamines"(pdf). Psychopharmacology Bulletin. 4 (3): 13. PMID 5615546.
  4. Cao, Yujin; Zhang, Haibo; Liu, Hui; Liu, Wei; Zhang, Rubing; Xian, Mo; Liu, Huizhou (2018-02-01). "Biosynthesis and production of sabinene: current state and perspectives". Applied Microbiology and Biotechnology. 102 (4): 1535–1544. doi:10.1007/s00253-017-8695-5. ISSN 1432-0614.
  5. Peters, R.J.; Croteau, R. B. (2003-09-15). "Alternative termination chemistries utilized by monoterpene cyclases: chimeric analysis of bornyl diphosphate, 1,8-cineole, and sabinene synthases". Archives of Biochemistry and Biophysics. 417 (2): 203–211. doi:10.1016/S0003-9861(03)00347-3. ISSN 0003-9861.
  6. Adam, K. P.; Croteau, R. (1998-09-28). "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". Phytochemistry. 49 (2): 475–480. doi:10.1016/S0031-9422(97)00741-3. ISSN 0031-9422.

Sabinene
Sabinene Language Watch Edit Sabinene is a natural bicyclic monoterpene with the molecular formula C10H16 It is isolated from the essential oils of a variety of plants including Marjoram 2 holm oak Quercus ilex and Norway spruce Picea abies It has a strained ring system with a cyclopentane ring fused to a cyclopropane ring Sabinene 1 NamesIUPAC name 4 methylene 1 1 methylethyl bicyclo 3 1 0 hexaneIdentifiersCAS Number 3387 41 5 Y10408 16 9 Y2009 00 9 Y3D model JSmol Interactive imageChEBI CHEBI 50027 YChEMBL ChEMBL452687 YChemSpider 17769 YECHA InfoCard 100 020 194KEGG C16777 YPubChem CID 18818UNII 7D1TL44GPC YI223NX31W9 YXYL0G8758O YCompTox Dashboard EPA DTXSID70863164InChI InChI 1S C10H16 c1 7 2 10 5 4 8 3 9 10 6 10 h7 9H 3 6H2 1 2H3 YKey NDVASEGYNIMXJL UHFFFAOYSA N YInChI 1 C10H16 c1 7 2 10 5 4 8 3 9 10 6 10 h7 9H 3 6H2 1 2H3Key NDVASEGYNIMXJL UHFFFAOYAWSMILES C C2C1CC1 C C C CC2PropertiesChemical formula C10H16Molar mass 136 23 g molDensity 0 844 g mL at 20 C g cm3Boiling point 163 to 164 C 325 to 327 F 436 to 437 K Except where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa Y verify what is Y N Infobox references Sabinene is one of the chemical compounds that contributes to the spiciness of black pepper 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 3 Laurus nobilis and Clausena anisata Biosynthesis EditSabinene a bicyclic monoterpene is present in the and enantiomers 4 It is biosynthesized from the common terpenoid precursor geranyl pyrophosphate GPP that undergoes polycyclization catalyzed by sabinene synthase SabS 4 5 GPP is formed from the terpenoid synthesis pathway with the starter units isopentenyl pyrophosphate IPP and dimethylallyl pyrophosphate DMAPP The starter units IPP and DMAPP can be synthesized from either the mevalonate MVA or the methylerythritol 4 phosphate MEP pathway 4 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 4 6 Further ionization and cyclization results in the formation of sabinene With the biosynthesis catalyzed by sabinene synthase the precursor geranyl pyrophosphate undergoes isomerization and cyclization to form sabinene 4 6 See also EditThujene a double bond isomer of sabineneReferences Edit Beilstein 5 IV 451 www tandfonline com doi abs 10 1080 0972060X 2014 935039 Shulgin A T Sargent T Naranjo C 1967 The Chemistry and Psychopharmacology of Nutmeg and of Several Related Phenylisopropylamines pdf Psychopharmacology Bulletin 4 3 13 PMID 5615546 a b c d e Cao Yujin Zhang Haibo Liu Hui Liu Wei Zhang Rubing Xian Mo Liu Huizhou 2018 02 01 Biosynthesis and production of sabinene current state and perspectives Applied Microbiology and Biotechnology 102 4 1535 1544 doi 10 1007 s00253 017 8695 5 ISSN 1432 0614 Peters R J Croteau R B 2003 09 15 Alternative termination chemistries utilized by monoterpene cyclases chimeric analysis of bornyl diphosphate 1 8 cineole and sabinene synthases Archives of Biochemistry and Biophysics 417 2 203 211 doi 10 1016 S0003 9861 03 00347 3 ISSN 0003 9861 a b Adam K P Croteau R 1998 09 28 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 Phytochemistry 49 2 475 480 doi 10 1016 S0031 9422 97 00741 3 ISSN 0031 9422 This article about a hydrocarbon is a stub You can help Wikipedia by expanding it vte Retrieved from https en wikipedia org w index php title Sabinene amp oldid 1053494919, wikipedia, wiki, book,

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