Geranyl geraniol

Structural formula
General
Surname	Geranyl geraniol
other names	all- trans -3,7,11-15-tetramethyl-2,6,10,14-hexadecatetraen-1-ol
Molecular formula	C 20 H 34 O
Brief description	colorless to light yellow liquid
External identifiers / databases
EC number	623-656-5
ECHA InfoCard	100.152.315
PubChem	5281365
Wikidata	Q3123708
properties
Molar mass	290.48 g mol −1
Physical state	liquid
density	0.89 g cm −3
boiling point	152-153 ° C (9.3 Pa)
solubility	soluble in ethanol, DMSO, chloroform, acetone and other solvents
Refractive index	1.4932 (30 ° C)
safety instructions
GHS labeling of hazardous substances Caution
H and P phrases	H: 315-319-335
	P: 261-305 + 351 + 338
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . Refractive index: Na-D line , 20 ° C

Geranylgeraniol is a chemical compound from the group of diterpenes .

Occurrence

Pale yellow bumblebee ( Bombus lucorum )

Geranylgeraniol is found in many plants, as well as some bacteria and insects - e.g. B. Light yellow bumblebee ( Bombus lucorum ) - before.

Extraction and presentation

Geranylgeraniol is formed in biosynthesis by the reaction of two isoprene units to geraniol .

properties

Geranylgeraniol is a colorless to light yellow clear liquid.

use

Geranylgeraniol is the metabolic precursor of many diterpenes and carotenoids . It comes in many compounds as well as a side chain of vitamin K before. In vitro studies of its derivative geranylgeranyl pyrophosphate showed that this is a potent and selective agent against Mycobacterium tuberculosis.

Web links

Insects that communicate with geranylgeraniol.

Individual evidence

↑ ^a ^b ^c ^d ^e ^f Data sheet geranylgeraniol, ≥85% (GC) from Sigma-Aldrich , accessed on May 13, 2015 ( PDF ).
↑ ^a ^b ^c ^d Burkhard Fugmann, Susanne Lang-Fugmann, Wolfgang Steglich: RÖMPP Encyclopedia Natural Products, 1st Edition, 2000 . Georg Thieme Verlag, 2014, ISBN 3-13-179311-2 , p. 258 ( limited preview in Google Book search).
↑ Santa Cruz Biotechnology: Geranylgeraniol , accessed May 14, 2015.
↑ ^a ^b Frank D. Gunstone, John L. Harwood, Fred B Padley: The Lipid Handbook, Second Edition . CRC Press, 1994, ISBN 978-0-412-43320-7 , pp. 526 ( limited preview in Google Book search).
↑ Axel Gloe, Norbert Pfennig: The occurrence of phytol and geranylgeraniol in the bacteriochlorophylls of red and green sulfur bacteria. In: Archives of Microbiology. 96, 1974, p. 93, doi : 10.1007 / BF00590166 .
^ E. David Morgan: Biosynthesis in Insects . Royal Society of Chemistry, 2010, ISBN 978-1-84755-808-4 , pp. 221 ( limited preview in Google Book search).

[Sigma-1] ↑ ^a ^b ^c ^d ^e ^f Data sheet geranylgeraniol, ≥85% (GC) from Sigma-Aldrich , accessed on May 13, 2015 ( PDF ).

[Burkhard_Fugmann,_Susanne_Lang-Fugmann,_Wolfgang_Steglich-2] Burkhard Fugmann, Susanne Lang-Fugmann, Wolfgang Steglich: RÖMPP Encyclopedia Natural Products, 1st Edition, 2000 . Georg Thieme Verlag, 2014, ISBN 3-13-179311-2 , p. 258 ( limited preview in Google Book search).

[sc-3] Santa Cruz Biotechnology: Geranylgeraniol , accessed May 14, 2015.

[Frank_D._Gunstone,_John_L._Harwood,_Fred_B._Padley-4] Frank D. Gunstone, John L. Harwood, Fred B Padley: The Lipid Handbook, Second Edition . CRC Press, 1994, ISBN 978-0-412-43320-7 , pp. 526 ( limited preview in Google Book search).

[DOI10.1007/BF00590166-5] Axel Gloe, Norbert Pfennig: The occurrence of phytol and geranylgeraniol in the bacteriochlorophylls of red and green sulfur bacteria. In: Archives of Microbiology. 96, 1974, p. 93, doi : 10.1007 / BF00590166 .

[E._David_Morgan-6] E. David Morgan: Biosynthesis in Insects . Royal Society of Chemistry, 2010, ISBN 978-1-84755-808-4 , pp. 221 ( limited preview in Google Book search).