48809

Sigma-Aldrich

Geranyllinalool

technical, ≥95% (GC)

Synonym(s):
3,7,11,15-Tetramethyl-1,6,10,14-hexadecatetraen-3-ol
Empirical Formula (Hill Notation):
C20H34O
CAS Number:
Molecular Weight:
290.48
Beilstein/REAXYS Number:
6713421
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

grade

technical

assay

≥95% (GC)

refractive index

n20/D 1.490

density

0.885 g/mL at 20 °C (lit.)

SMILES string

C\C(C)=C/CC\C(C)=C\CC\C(C)=C\CCC(C)(O)C=C

InChI

1S/C20H34O/c1-7-20(6,21)16-10-15-19(5)14-9-13-18(4)12-8-11-17(2)3/h7,11,13,15,21H,1,8-10,12,14,16H2,2-6H3/b18-13+,19-15+

InChI key

IQDXAJNQKSIPGB-HQSZAHFGSA-N

General description

Geranyllinalool is a diterpene alcohol, commonly used as a fragrant. It imparts insecticidal property to xylophagous insects and pine wood.

Application

Geranyllinalool has been used in studying its influence on pyocyanin and Pseudomonas quinolone signal (PQS) production by Pseudomonas aeruginosa. It may be used as a starting material in the synthesis of teprenone by reacting with acetylated Meldrum′s acid.

Packaging

1 mL in glass bottle

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Precautionary Statements

Target Organs

Respiratory system

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

NONH for all modes of transport

WGK Germany

WGK 2

Flash Point(F)

354.2 °F - closed cup

Flash Point(C)

179 °C - closed cup

Certificate of Analysis
Certificate of Origin
A Lapczynski et al.
Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association, 46 Suppl 11, S176-S178 (2008-07-22)
A toxicologic and dermatologic review of geranyl linalool when used as a fragrance ingredient is presented.
Cinzia Formighieri et al.
Applied microbiology and biotechnology, 101(7), 2791-2800 (2017-01-08)
Cyanobacteria are industrially robust photosynthetic microorganisms that can be genetically programmed to synthesize commodity products for domestic and industrial consumption. In the present work, Synechocystis was endowed with the synthesis of the plant secondary metabolite geranyllinalool, a diterpene alcohol of...
Elsa Youngsteadt et al.
PloS one, 5(12), e15822-e15822 (2011-01-07)
In lowland Amazonian rainforests, specific ants collect seeds of several plant species and cultivate them in arboreal carton nests, forming species-specific symbioses called ant-gardens (AGs). In this obligate mutualism, ants depend on the plants for nest stability and the plants...
Jiao Xie et al.
Food chemistry, 243, 269-276 (2017-11-18)
Oleocellosis is a serious physiological disorder in citrus fruit that mainly results in appearance and quality deterioration. It has been well established that the occurrence of oleocellosis is highly correlated with the release of peel oil from citrus fruit, while...
Diketene and Acetylated Meldrum's Acid: Agents for a Facile Teprenone Synthesis via Carroll Rearrangement.
De Castro KA, et al.
Bull. Korean Chem. Soc., 30(9), 2155-2157 (2009)

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