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Wikipedia

Geranylgeraniol

Geranylgeraniol is a diterpenoid alcohol. It is a colorless waxy solid.[1]

Geranylgeraniol
Names
Preferred IUPAC name
(2E,6E,10E)-3,7,11,15-Tetramethylhexadeca-2,6,10,14-tetraen-1-ol
Other names
Tetraprenol
Identifiers
  • 7614-21-3 Y
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:46762
ChemSpider
  • 4444726
ECHA InfoCard 100.152.315
  • 5281365
UNII
  • AIA02AJA3A Y
  • InChI=1S/C20H34O/c1-17(2)9-6-10-18(3)11-7-12-19(4)13-8-14-20(5)15-16-21/h9,11,13,15,21H,6-8,10,12,14,16H2,1-5H3/b18-11+,19-13+,20-15+
    Key: OJISWRZIEWCUBN-QIRCYJPOSA-N
  • InChI=1/C20H34O/c1-17(2)9-6-10-18(3)11-7-12-19(4)13-8-14-20(5)15-16-21/h9,11,13,15,21H,6-8,10,12,14,16H2,1-5H3/b18-11+,19-13+,20-15+
    Key: OJISWRZIEWCUBN-QIRCYJPOBA
  • OC/C=C(/CC/C=C(/CC\C=C(/C)CC\C=C(/C)C)C)C
Properties
C20H34O
Molar mass 290.491 g·mol−1
Appearance Clear liquid
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Geranylgeraniol is an important intermediate in the biosynthesis of other diterpenes, of vitamins E, and of K.[2] It also used in the post-translational modification known as geranylgeranylation. Geranylgeraniol is a pheromone for bumblebees and a variety of other insects.[3]

Geranylgeraniol is a potent inhibitor of Mycobacterium tuberculosis in vitro.[4]

See also edit

References edit

  1. ^ Jin, Yinghua; Roberts, Frank G.; Coates, Robert M. (2007). "Stereoselective Isoprenoid Chain Extension with Acetoacetate Dianion: [(E, E, E)-Geranylgeraniol from (E, E)-Farnesol". Organic Syntheses. 84: 43. doi:10.15227/orgsyn.084.0043.
  2. ^ Fatty alcohols 2012-06-25 at the Wayback Machine, cyberlipid.org
  3. ^ Semiochemical - geranylgeraniol, pherobase.com
  4. ^ Vik, A; James, A; Gundersen, LL (2007). "Screening of terpenes and derivatives for antimycobacterial activity; identification of geranylgeraniol and geranylgeranyl acetate as potent inhibitors of Mycobacterium tuberculosis in vitro". Planta Medica. 73 (13): 1410–2. doi:10.1055/s-2007-990238. PMID 17924309.

geranylgeraniol, diterpenoid, alcohol, colorless, waxy, solid, names, preferred, iupac, name, tetramethylhexadeca, tetraen, other, names, tetraprenol, identifiers, number, 7614, model, jsmol, interactive, image, chebi, chebi, 46762, chemspider, 4444726, echa, . Geranylgeraniol is a diterpenoid alcohol It is a colorless waxy solid 1 Geranylgeraniol Names Preferred IUPAC name 2E 6E 10E 3 7 11 15 Tetramethylhexadeca 2 6 10 14 tetraen 1 ol Other names Tetraprenol Identifiers CAS Number 7614 21 3 Y 3D model JSmol Interactive image ChEBI CHEBI 46762 ChemSpider 4444726 ECHA InfoCard 100 152 315 PubChem CID 5281365 UNII AIA02AJA3A Y InChI InChI 1S C20H34O c1 17 2 9 6 10 18 3 11 7 12 19 4 13 8 14 20 5 15 16 21 h9 11 13 15 21H 6 8 10 12 14 16H2 1 5H3 b18 11 19 13 20 15 Key OJISWRZIEWCUBN QIRCYJPOSA NInChI 1 C20H34O c1 17 2 9 6 10 18 3 11 7 12 19 4 13 8 14 20 5 15 16 21 h9 11 13 15 21H 6 8 10 12 14 16H2 1 5H3 b18 11 19 13 20 15 Key OJISWRZIEWCUBN QIRCYJPOBA SMILES OC C C CC C C CC C C C CC C C C C C C Properties Chemical formula C 20H 34O Molar mass 290 491 g mol 1 Appearance Clear liquid Except where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa Infobox references Geranylgeraniol is an important intermediate in the biosynthesis of other diterpenes of vitamins E and of K 2 It also used in the post translational modification known as geranylgeranylation Geranylgeraniol is a pheromone for bumblebees and a variety of other insects 3 Geranylgeraniol is a potent inhibitor of Mycobacterium tuberculosis in vitro 4 See also editGeranylgeranyl pyrophosphateReferences edit Jin Yinghua Roberts Frank G Coates Robert M 2007 Stereoselective Isoprenoid Chain Extension with Acetoacetate Dianion E E E Geranylgeraniol from E E Farnesol Organic Syntheses 84 43 doi 10 15227 orgsyn 084 0043 Fatty alcohols Archived 2012 06 25 at the Wayback Machine cyberlipid org Semiochemical geranylgeraniol pherobase com Vik A James A Gundersen LL 2007 Screening of terpenes and derivatives for antimycobacterial activity identification of geranylgeraniol and geranylgeranyl acetate as potent inhibitors of Mycobacterium tuberculosis in vitro Planta Medica 73 13 1410 2 doi 10 1055 s 2007 990238 PMID 17924309 Retrieved from https en wikipedia org w index php title Geranylgeraniol amp oldid 1105117646, wikipedia, wiki, book, books, library,

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