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.

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

Número CAS 28387-44-2^[1]

ChemSpider 29776407

Datos rápidos Nombre IUPAC, General ...

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
SMILES C/C/1=C\CC/C(=C/C[C@H](CC1)C(C)C)/C
InChI 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/m³; 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.
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Cerrar

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

Número CAS 37839-63-7^[2]

ChemSpider 28288426

Datos rápidos Nombre IUPAC, General ...

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
SMILES C/C/1=C/CCC(=C)/C=C\[C@@H](CC1)C(C)C
InChI 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.
[editar datos en Wikidata]

Cerrar

Estructuras


Germacreno A	Germacreno B	Germacreno C	Germacreno D	Germacreno 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.

Estructuras

Producción natural

Referencias

Germacreno A

Germacreno D

Enlaces externos

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