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Germacreno

Germacrenos son una clase de hidrocarburos orgánicos volátiles, específicamente, sesquiterpenos . Germacrenos se producen típicamente en un número de especies de plantas por sus propiedades antimicrobianas e insecticidas, aunque también desempeñan un papel como feromonas de insectos. Dos moléculas prominentes son germacreno A y germacreno D.

 
Germacreno A
Nombre IUPAC
(1E,5E,8S)-1,5-dimethyl-8-(prop-1-en-2-yl)cyclodeca-1,5-diene
General
Otros nombres

(-)-Germacrene A Germacra-3,9,11-triene, (E,E)- 1,5-cyclodecadiene, 1,5-dimethyl-8-(1-methylethenyl)-, (1E,5E,8S)- 1,5-cyclodecadiene, 1,5-dimethyl-8-(1-methylethenyl)-,

(S-(E,E))-
Fórmula molecular C15H24
Identificadores
Número CAS 28387-44-2[1]
ChemSpider 29776407
C/C/1=C\CC/C(=C/C[C@H](CC1)C(C)C)/C
InChI=1S/C15H26/c1-12(2)15-10-8-13(3)6-5-7-14(4)9-11-15/h6,9,12,15H,5,7-8,10-11H2,1-4H3/b13-6+,14-9+/t15-/m0/s1
Key: YDLBHMSVYMFOMI-SDFJSLCBSA-N
Propiedades físicas
Densidad 0,793 kg/; 0,000793 g/cm³
Masa molar 204.35 g/mol
Punto de ebullición 236,4 °C (510 K)
Valores en el SI y en condiciones estándar
(25 y 1 atm), salvo que se indique lo contrario.
 
Germacreno D
Nombre IUPAC
(S,1Z,6Z)-8-isopropyl-1-methyl-5-methylenecyclodeca-1,6-diene
General
Otros nombres

1-methyl-5-methylene-8-(1-methylethyl)-1,6-cyclodecadiene

1,6-cyclodecadiene, 1-methyl-5-methylene-8-(1-methylethyl)-
Fórmula molecular C15H24
Identificadores
Número CAS 37839-63-7[2]
ChemSpider 28288426
C/C/1=C/CCC(=C)/C=C\[C@@H](CC1)C(C)C
InChI=1S/C15H24/c1-12(2)15-10-8-13(3)6-5-7-14(4)9-11-15/h7-8,10,12,15H,3,5-6,9,11H2,1-2,4H3/b10-8-,14-7-/t15-/m0/s1
Key: GAIBLDCXCZKKJE-ACWLMNNXSA-N
Propiedades físicas
Masa molar 204.35 g/mol
Valores en el SI y en condiciones estándar
(25 y 1 atm), salvo que se indique lo contrario.

Estructuras

         
Germacrene A Germacrene B Germacrene C Germacrene D Germacrene E

Producción natural

El aceite esencial de la ortiga muerta roja (Lamium purpureum) se caracteriza por su alto contenido de germacreno D,[3]​ así como Clausena anisata.

Referencias

  1. Número CAS
  2. Número CAS
  3. Flamini G, Cioni PL, Morelli I (2005). «Composition of the essential oils and in vivo emission of volatiles of four Lamium species from Italy: L. purpureum, L. hybridum, L. bifidum and L. amplexicaule». Food Chemistry 91 (1): 63-68. doi:10.1016/j.foodchem.2004.05.047. 
  • Adio AM (2009). «Germacrenes A–E and related compounds: thermal, photochemical and acid induced transannular cyclizations». Tetrahedron 65 (8): 1533-1552. doi:10.1016/j.tet.2008.11.050. 

Germacreno A

  • Deguerry F, Pastore L, Wu S, Clark A, Chappell J, Schalk M. The diverse sesquiterpene profile of patchouli, Pogostemon cablin, is correlated with a limited number of sesquiterpene synthases. Arch Biochem Biophys. 2006 Oct 15;454(2):123-36.
  • Omura H, Honda K, Feeny P. From terpenoids to aliphatic acids: further evidence for late-instar switch in osmeterial defense as a characteristic trait of swallowtail butterflies in the tribe papilionini. J Chem Ecol. 2006 Sep;32(9):1999-2012.
  • Forcat S, Allemann RK. Stabilisation of transition states prior to and following eudesmane cation in aristolochene synthase. Org Biomol Chem. 2006 Jul 7;4(13):2563-7.
  • Bertea CM, Voster A, Verstappen FW, Maffei M, Beekwilder J, Bouwmeester HJ. Isoprenoid biosynthesis in Artemisia annua: cloning and heterologous expression of a germacrene A synthase from a glandular trichome cDNA library. Arch Biochem Biophys. 2006 Apr 15;448(1-2):3-12.
  • Lou Y, Baldwin IT. Silencing of a germin-like gene in Nicotiana attenuata improves performance of native herbivores. Plant Physiol. 2006 Mar;140(3):1126-36.
  • Chang YJ, Jin J, Nam HY, Kim SU. Point mutation of (+)-germacrene A synthase from Ixeris dentata. Biotechnol Lett. 2005 Mar;27(5):285-8.

Germacreno D

  • Rivero-Cruz B, Rivero-Cruz I, Rodríguez JM, Cerda-Garcia-Rojas CM, Mata R. Qualitative and quantitative analysis of the active components of the essential oil from Brickellia veronicaefolia by nuclear magnetic resonance spectroscopy. J Nat Prod. 2006 Aug;69(8):1172-6.
  • Yang FQ, Li SP, Chen Y, Lao SC, Wang YT, Dong TT, Tsim KW. Identification and quantitation of eleven sesquiterpenes in three species of Curcuma rhizomes by pressurized liquid extraction and gas chromatography-mass spectrometry. J Pharm Biomed Anal. 2005 Sep 15;39(3-4):552-8.
  • Umlauf D, Zapp J, Becker H, Adam KP. Biosynthesis of the irregular monoterpene artemisia ketone, the sesquiterpene germacrene D and other isoprenoids in Tanacetum vulgare L. (Asteraceae). Phytochemistry. 2004 Sep;65(17):2463-70.
  • Agnihotri VK, Thappa RK, Meena B, Kapahi BK, Saxena RK, Qazi GN, Agarwal SG. Essential oil composition of aerial parts of Angelica glauca growing wild in North-West Himalaya (India). Phytochemistry. 2004 Aug;65(16):2411-3.
  • Raal A, Paaver U, Arak E, Orav A. Content and composition of the essential oil of Thymus serpyllum L. growing wild in Estonia. Medicina (Kaunas). 2004;40(8):795-800.
  • He X, Cane DE. Mechanism and stereochemistry of the germacradienol/germacrene D synthase of Streptomyces coelicolor A3(2). J Am Chem Soc. 2004 Mar 10;126(9):2678-9.
  • Arimura, G-I., Huber, DPW, Bohlmann, J. Forest tent caterpillars (Malacosoma disstria) induce local and systemic diurnal emissions of terpenoid volátiles in hybrid poplar (Populus trichocarpa x deltoides): cDNA cloning, functional characterization, and patterns of gene expression of (-)-germacrene D synthase, PtdTPS1. The Plant Journal 2004 37: 603-616.

Enlaces externos

  •   Datos: Q5550970
  •   Multimedia: Germacrenes / Q5550970

germacreno, clase, hidrocarburos, orgánicos, volátiles, específicamente, sesquiterpenos, producen, típicamente, número, especies, plantas, propiedades, antimicrobianas, insecticidas, aunque, también, desempeñan, papel, como, feromonas, insectos, moléculas, pro. Germacrenos son una clase de hidrocarburos organicos volatiles especificamente sesquiterpenos Germacrenos se producen tipicamente en un numero de especies de plantas por sus propiedades antimicrobianas e insecticidas aunque tambien desempenan un papel como feromonas de insectos Dos moleculas prominentes son germacreno A y germacreno D Germacreno ANombre IUPAC 1E 5E 8S 1 5 dimethyl 8 prop 1 en 2 yl cyclodeca 1 5 dieneGeneralOtros nombres Germacrene A Germacra 3 9 11 triene E E 1 5 cyclodecadiene 1 5 dimethyl 8 1 methylethenyl 1E 5E 8S 1 5 cyclodecadiene 1 5 dimethyl 8 1 methylethenyl S E E Formula molecularC15H24IdentificadoresNumero CAS28387 44 2 1 ChemSpider29776407SMILESC C 1 C CC C C C C H CC1 C C C CInChIInChI 1S C15H26 c1 12 2 15 10 8 13 3 6 5 7 14 4 9 11 15 h6 9 12 15H 5 7 8 10 11H2 1 4H3 b13 6 14 9 t15 m0 s1 Key YDLBHMSVYMFOMI SDFJSLCBSA NPropiedades fisicasDensidad0 793 kg m 0 000793 g cm Masa molar204 35 g molPunto de ebullicion236 4 C 510 K Valores en el SI y en condiciones estandar 25 y 1 atm salvo que se indique lo contrario editar datos en Wikidata Germacreno DNombre IUPAC S 1Z 6Z 8 isopropyl 1 methyl 5 methylenecyclodeca 1 6 dieneGeneralOtros nombres1 methyl 5 methylene 8 1 methylethyl 1 6 cyclodecadiene 1 6 cyclodecadiene 1 methyl 5 methylene 8 1 methylethyl Formula molecularC15H24IdentificadoresNumero CAS37839 63 7 2 ChemSpider28288426SMILESC C 1 C CCC C C C C H CC1 C C CInChIInChI 1S C15H24 c1 12 2 15 10 8 13 3 6 5 7 14 4 9 11 15 h7 8 10 12 15H 3 5 6 9 11H2 1 2 4H3 b10 8 14 7 t15 m0 s1 Key GAIBLDCXCZKKJE ACWLMNNXSA NPropiedades fisicasMasa molar204 35 g molValores en el SI y en condiciones estandar 25 y 1 atm salvo que se indique lo contrario editar datos en Wikidata Indice 1 Estructuras 2 Produccion natural 3 Referencias 3 1 Germacreno A 3 2 Germacreno D 4 Enlaces externosEstructuras Editar Germacrene A Germacrene B Germacrene C Germacrene D Germacrene EProduccion natural EditarEl aceite esencial de la ortiga muerta roja Lamium purpureum se caracteriza por su alto contenido de germacreno D 3 asi como Clausena anisata Referencias Editar Numero CAS Numero CAS Flamini G Cioni PL Morelli I 2005 Composition of the essential oils and in vivo emission of volatiles of four Lamium species from Italy L purpureum L hybridum L bifidum and L amplexicaule Food Chemistry 91 1 63 68 doi 10 1016 j foodchem 2004 05 047 Adio AM 2009 Germacrenes A E and related compounds thermal photochemical and acid induced transannular cyclizations Tetrahedron 65 8 1533 1552 doi 10 1016 j tet 2008 11 050 Germacreno A Editar Deguerry F Pastore L Wu S Clark A Chappell J Schalk M The diverse sesquiterpene profile of patchouli Pogostemon cablin is correlated with a limited number of sesquiterpene synthases Arch Biochem Biophys 2006 Oct 15 454 2 123 36 Omura H Honda K Feeny P From terpenoids to aliphatic acids further evidence for late instar switch in osmeterial defense as a characteristic trait of swallowtail butterflies in the tribe papilionini J Chem Ecol 2006 Sep 32 9 1999 2012 Forcat S Allemann RK Stabilisation of transition states prior to and following eudesmane cation in aristolochene synthase Org Biomol Chem 2006 Jul 7 4 13 2563 7 Bertea CM Voster A Verstappen FW Maffei M Beekwilder J Bouwmeester HJ Isoprenoid biosynthesis in Artemisia annua cloning and heterologous expression of a germacrene A synthase from a glandular trichome cDNA library Arch Biochem Biophys 2006 Apr 15 448 1 2 3 12 Lou Y Baldwin IT Silencing of a germin like gene in Nicotiana attenuata improves performance of native herbivores Plant Physiol 2006 Mar 140 3 1126 36 Chang YJ Jin J Nam HY Kim SU Point mutation of germacrene A synthase from Ixeris dentata Biotechnol Lett 2005 Mar 27 5 285 8 Germacreno D Editar Rivero Cruz B Rivero Cruz I Rodriguez JM Cerda Garcia Rojas CM Mata R Qualitative and quantitative analysis of the active components of the essential oil from Brickellia veronicaefolia by nuclear magnetic resonance spectroscopy J Nat Prod 2006 Aug 69 8 1172 6 Yang FQ Li SP Chen Y Lao SC Wang YT Dong TT Tsim KW Identification and quantitation of eleven sesquiterpenes in three species of Curcuma rhizomes by pressurized liquid extraction and gas chromatography mass spectrometry J Pharm Biomed Anal 2005 Sep 15 39 3 4 552 8 Umlauf D Zapp J Becker H Adam KP Biosynthesis of the irregular monoterpene artemisia ketone the sesquiterpene germacrene D and other isoprenoids in Tanacetum vulgare L Asteraceae Phytochemistry 2004 Sep 65 17 2463 70 Agnihotri VK Thappa RK Meena B Kapahi BK Saxena RK Qazi GN Agarwal SG Essential oil composition of aerial parts of Angelica glauca growing wild in North West Himalaya India Phytochemistry 2004 Aug 65 16 2411 3 Raal A Paaver U Arak E Orav A Content and composition of the essential oil of Thymus serpyllum L growing wild in Estonia Medicina Kaunas 2004 40 8 795 800 He X Cane DE Mechanism and stereochemistry of the germacradienol germacrene D synthase of Streptomyces coelicolor A3 2 J Am Chem Soc 2004 Mar 10 126 9 2678 9 Arimura G I Huber DPW Bohlmann J Forest tent caterpillars Malacosoma disstria induce local and systemic diurnal emissions of terpenoid volatiles in hybrid poplar Populus trichocarpa x deltoides cDNA cloning functional characterization and patterns of gene expression of germacrene D synthase PtdTPS1 The Plant Journal 2004 37 603 616 Enlaces externos EditarEsta obra contiene una traduccion derivada de Germacrene de Wikipedia en ingles publicada por sus editores bajo la Licencia de documentacion libre de GNU y la Licencia Creative Commons Atribucion CompartirIgual 3 0 Unported Datos Q5550970 Multimedia Germacrenes Q5550970 Obtenido de https es wikipedia org w index php title Germacreno amp oldid 143477539, wikipedia, wiki, leyendo, leer, libro, biblioteca,

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