51446-64-1

Basic information

• Product Name: geranylcitronellol
• Synonyms: geranylcitronellol
• CAS NO: 51446-64-1
• Molecular Formula: C20H36 O
• Molecular Weight: 292.5
• Mol File: 51446-64-1.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 388.2°Cat760mmHg
• Flash Point: 121.7°C
• Appearance: /
• Density: 0.868g/cm³
• Vapor Pressure: 1.25E-07mmHg at 25°C
• Refractive Index: 1.481
• CAS DataBase Reference: geranylcitronellol(CAS DataBase Reference)
• NIST Chemistry Reference: geranylcitronellol(51446-64-1)
• EPA Substance Registry System: geranylcitronellol(51446-64-1)

Safety Data

• Hazardous Substances Data: 51446-64-1(Hazardous Substances Data)

Usage

Uses

Geranylcitronellol is an isoprenoid pheromone produced in bumblebee males.

InChI:InChI=1/C20H36O/c1-17(2)9-6-10-18(3)11-7-12-19(4)13-8-14-20(5)15-16-21/h9,11,13,20-21H,6-8,10,12,14-16H2,1-5H3/b18-11+,19-13+

Upstream product

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• 56881-52-8 (Z)-(3,7-dimethylocta-2,6-diene-1-sulfonyl)benzene 
• 25996-10-5 (Z)-neryl bromide 
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• 281661-30-1 (S)-tert-butyl (3,7-dimethyloct-6-enyloxy)diphenylsilane 
• 113219-28-6 (E,E)-4,8,12-Trimethyl-3,7,11-tridecatrien-1-yl iodide 
• 1026097-95-9 (6E,10E)-(S)-3,7,11,15-Tetramethyl-hexadeca-6,10,14-trienoic acid (1R,2S,4R)-1,7,7-trimethyl-2-naphthalen-2-yl-bicyclo[2.2.1]hept-2-yl ester 
• 105999-94-8 1-(R)-endo-phenylbornyl E-butenoate 
• 24034-73-9 Geranylgeraniol 
• 124870-07-1 (1E,5E)-1-iodo-2,6,10-trimethyl-1,5,9-undecatriene 
• 22850-55-1 (E)-6,10-dimethyl-5,9-undecadien-1-yne 
• 6138-90-5 trans-geranyl bromide 
• 36237-72-6 (6E,10E)-(R)-3,7,11,15-Tetramethyl-hexadeca-6,10,14-trienoic acid methyl ester 

Relevant articles and documents

A Unified Approach for the Total Synthesis of cyclo-Archaeol, iso-Caldarchaeol, Caldarchaeol, and Mycoketide

Ir-catalyzed asymmetric alkene hydrogenation is presented as the strategy par excellence to prepare saturated isoprenoids and mycoketides. This highly stereoselective synthesis approach is combined with an established 13C-NMR method to determine the enantioselectivity of each methyl-branched stereocenter. It is shown that this analysis is fit for purpose and the combination allows the synthesis of the title compounds with a significant increase in efficiency.

Characterization of the single-subunit oligosaccharyltransferase STT3A from Trypanosoma brucei using synthetic peptides and lipid-linked oligosaccharide analogs

The initial transfer of a complex glycan in protein N-glycosylation is catalyzed by oligosaccharyltransferase (OST), which is generally a multisubunit membrane protein complex in the endoplasmic reticulum but a single-subunit enzyme (ssOST) in some protists. To investigate the reaction mechanism of ssOST, we recombinantly expressed, purified and characterized the STT3A protein from Trypanosoma brucei (TbSTT3A). We analyzed the in vitro activity of TbSTT3A by synthesizing fluorescently labeled acceptor peptides as well as lipid-linked oligosaccharide (LLO) analogs containing a chitobiose moiety coupled to oligoprenyl carriers of distinct lengths (C10, C15, C20 and C25) and with different double bond stereochemistry. We found that in addition to proline, charged residues at the +1 position of the sequon inhibited glycan transfer. An acidic residue at the -2 position significantly increased catalytic turnover but was not essential, in contrast to the bacterial OST. While all synthetic LLO analogs were processed by TbSTT3A, the length of the polyprenyl tail, but not the stereochemistry of the double bonds, determined their apparent affinity. We also synthesized phosphonate analogs of the LLOs, which were found to be competitive inhibitors of the reaction, although with lower apparent affinity to TbSTT3A than the active pyrophosphate analogs.

Analysis of the labial gland secretion of the cuckoo-bumblebee (Psithyrus vestalis) males and synthesis of abundant geranylcitronellol

Labial glands of the cuckoo-bumblebee males of the species Psithyrus vestalis were extracted and the components of their secretions were identified. Chemical composition of the males' signal of Psithyrus vestalis has not yet been described in the literatu