게르마크렌

Germacrene
게르마크렌 A
Germacrene A chemical structure.png
이름
IUPAC 이름
(1E,5E,8S)-1,5-디메틸-8-(prop-1-en-2-yl)사이클로데카-1,5-diene
기타 이름
  • (--제르매크렌 A)
  • (E,E)-제르마크라-3,9,11-트리엔
  • (1E,5E,8S)-1,5-디메틸-8-(1-메틸테닐)-1,5-사이클로데카디엔
  • (S-(E,E)-1,5-디메틸-8-(1-메틸테닐)-1,5-사이클로데카디엔
식별자
  • 28387-44-2 checkY
  • B: 15423-57-1
  • C: 34323-15-4
  • D: 37839-63-7
3D 모델(JSmol)
6500908 (A) 1864177 (D)
체비
켐벨
켐스파이더
케그
펍켐 CID
  • 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 ☒N
    키: YDLBHMSVYMFOMI-SDFJSLCBSA-N ☒N
  • InChi=1/C15H26/c1-12(2)15-10-8-13(3)6-5-7-14(4)9-15/h6,9,12,15H,5,7-8,10-11H2,1-4H3/b13-6+,14-9+/t15-m0/m0/s1
    키: YDLBHMSVYMFOMI-SDFJSLCBBV
  • A: InChI=1S/C15H24/c1-12(2)15-10-8-13(3)6-5-7-14(4)9-11-15/h6,9,15H,1,5,7-8,10-11H2,2-4H3/b13-6+,14-9+/t15-/m1/s1
    키: XMRKUJJDDCUHV-DFSVIBJJSA-N
  • D: InChi=1S/C15H24/c1-12(2)15-10-8-13(3)6-5-7-14-14(3)/h7-8,10,12,15H,15H,5-6,9,11H2,1-2,4H3/b10-8,147
    키: GAIBLDCXCZKJE-BZX뤄임사-N
  • E: InChi=1S/C15H24/c1-12(2)15-10-8-13(3)6-5-7-14-14-15/h6,9,11,14-15H,1,5,7-8,10H2,2-4H3/b11-9+,136+
    키: OAOGSSSAAVUPEKA-BMCYRRCSA-N
  • C/C/1=C\CC/C(=C/C[@H](CC1)C(C)/C)
  • A: C/C/1=C\CC/C(=C/C[@H](CC1)C(=C)/C
  • B: C/C/1=C\CC/C(=C(C)C)1)/C
  • C: C/C/1=C\CC/C(=C/C=C(\CC1)/C(C)/C
  • E: CC\1CC/C=C(/C=C1)C(=C)C(=C)C)\c
특성.
C15H24
어금질량 204.35 g/190
밀도 0.793 g/mL
비등점 236.4°C(457.5°F, 509.5K)
달리 명시된 경우를 제외하고, 표준 상태(25°C [77°F], 100 kPa)의 재료에 대한 데이터가 제공된다.
☒ NVERIFI (?란checkY☒N?
Infobox 참조 자료
게르마크렌 D
Germacrene D chemical structure.png
이름
IUPAC 이름
(S,1Z,6Z)-8-이소프로필-1-메틸-5-메틸리덴사이클로데카-1,6-다이엔
기타 이름
1-메틸-5-메틸렌-8-(1-메틸레틸)-1,6-사이클로데카디엔
식별자
  • 37839-63-7
3D 모델(JSmol)
켐스파이더
펍켐 CID
  • 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
    키: GAIBLDCXCZKJE-ACWLMNXSA-N
  • InChI=1/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
    키: GAIBLDCXCZKJE-ACWMNNXBY
  • C/C/1=C/CCC(=C)/C=C\[C@H](CC1)C(C)C
특성.
C15H24
어금질량 204.35 g/190
달리 명시된 경우를 제외하고, 표준 상태(25°C [77°F], 100 kPa)의 재료에 대한 데이터가 제공된다.
Infobox 참조 자료

Germacrenes는 휘발성 유기 탄화수소의 한 종류, 특히 세스키테르펜이다. 제르마크레네는 곤충 페로몬의 역할도 하지만 항균성과 살충성을 위해 많은 식물 종에서 생산된다. 두 개의 두드러진 분자는 제르마크렌 A와 제르마크렌 D이다.

구조물들

게르마크렌은 5개의 이소머를 가지고 있다.

게르마크렌 이소머스
Germacrene A Germacrene B Germacrene C Germacrene D Germacrene E
게르마크렌 A 게르마크렌 B 게르마크렌 C 게르마크렌 D 게르마크렌 E

자연발생

붉은 데드네틀(Lamium purpleum)[1]과 헤지네틀(Genus Stachys)[2]의 에센셜 오일은 클라우세나 아니사타처럼 게르마크렌 D의 함량이 높은 것이 특징이다.

참조

  1. ^ Flamini, G.; Cioni, P. L.; 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.
  2. ^ Morteza‐Semnani, K.; Akbarzadeh, M.; Changizi, Sh. (2005-11-01). "Essential oils composition of Stachys byzantina, S. inflata, S. lavandulifolia and S. laxa from Iran". Flavour and Fragrance Journal. 21 (2): 300–303. doi:10.1002/ffj.1594.

추가 읽기

일반

  • Adio, A. M. (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.

게르마크렌 A

  • Deguerry, F.; Pastore, L.; Wu, S.; Clark, A.; Chappell, J.; Schalk, M. (2006-10-15). "The diverse sesquiterpene profile of patchouli, Pogostemon cablin, is correlated with a limited number of sesquiterpene synthases". Archives of Biochemistry and Biophysics. 454 (2): 123–136.
  • Omura, H.; Honda, K.; Feeny, P. (2006-09-01). "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". Journal of Chemical Ecology. 32 (9): 1999–2012.
  • Forcat, S.; Allemann, R. K. (2006-07-07). "Stabilisation of transition states prior to and following eudesmane cation in aristolochene synthase". Organic and Biomolecular Chemistry. 4 (13): 2563–2567.
  • Bertea, C. M.; Voster, A.; Verstappen, F. W.; Maffei, M.; Beekwilder, J.; Bouwmeester, H. J. (2006-04-15). "Isoprenoid biosynthesis in Artemisia annua: cloning and heterologous expression of a germacrene A synthase from a glandular trichome cDNA library". Archives of Biochemistry and Biophysics. 448 (1–2): 3–12.
  • Lou, Y; Baldwin, I. T. (2006-03-01). "Silencing of a germin-like gene in Nicotiana attenuata improves performance of native herbivores". Plant Physiology. 140 (3): 1126–1136.
  • Chang, Y.-J.; Jin, J.; Nam, H.-Y.; Kim, S.-U. (2005-03-01). "Point mutation of (+)-germacrene A synthase from Ixeris dentata". Biotechnology Letters. 27 (5): 285–288.

게르마크렌 D

  • Rivero Cruz, B.; Rivero Cruz, I; Rodríguez, J. M.; Cerda García-Rojas, C. M.; Mata, R. (2006-08-01). "Qualitative and quantitative analysis of the active components of the essential oil from 'Brickellia veronicaefolia by nuclear magnetic resonance spectroscopy". Journal of Natural Products. 69 (8): 1172–1176.
  • Yang, F.-Q.; Li, S.-P.; Chen, Y.; Lao, S.-C.; Wang, Y.-T.; Dong, T.-T.; Tsim, K.-W. (2005-09-15). "Identification and quantitation of eleven sesquiterpenes in three species of Curcuma rhizomes by pressurized liquid extraction and gas chromatography-mass spectrometry". Journal of Pharmaceutical and Biomedical Analysis. 39 (3–4): 552–558.
  • Umlauf, D.; Zapp, J.; Becker, H.; Adam, K. P. (2004-09-01). "Biosynthesis of the irregular monoterpene artemisia ketone, the sesquiterpene germacrene D and other isoprenoids in Tanacetum vulgare L. (Asteraceae)". Phytochemistry. 65 (17): 2463–2470.
  • Agnihotri, V. K.; Thappa, R. K.; Meena, B.; Kapahi, B. K.; Saxena, R. K.; Qazi, G. N.; Agarwal, S. G. (2004-08-01). "Essential oil composition of aerial parts of Angelica glauca growing wild in North-West Himalaya (India)". Phytochemistry. 65 (16): 2411–2413.
  • Raal, A.; Paaver, U.; Arak, E.; Orav, A. (2004). "Content and composition of the essential oil of Thymus serpyllum L. growing wild in Estonia". Medicina (Kaunas). 40 (8): 795–800.
  • He, X.; Cane, D. E. (2004-03-10). "Mechanism and stereochemistry of the germacradienol/germacrene D synthase of Streptomyces coelicolor A3(2)". Journal of the American Chemical Society. 126 (9): 2678–2679.
  • Arimura, G.-I.; Huber, D. P. W.; Bohlmann, J. (2004). "Forest tent caterpillars (Malacosoma disstria) induce local and systemic diurnal emissions of terpenoid volatiles in hybrid poplar (Populus trichocarpa × deltoides): cDNA cloning, functional characterization, and patterns of gene expression of (−)-germacrene D synthase, PtdTPS1". The Plant Journal. 37: 603–616.