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48809

Sigma-Aldrich

Geranyllinalool

technical, ≥90% (GC)

Synonym(s):

3,7,11,15-Tetramethyl-1,6,10,14-hexadecatetraen-3-ol

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About This Item

Empirical Formula (Hill Notation):
C20H34O
CAS Number:
1113-21-9
Molecular Weight:
290.48
Beilstein/REAXYS Number:
6713421
EC Number:
214-201-8
MDL number:
MFCD00059363
UNSPSC Code:
12352100
PubChem Substance ID:
329757417
NACRES:
NA.22

grade

technical

Quality Level

100

assay

≥90% (GC)

refractive index

n20/D 1.490

density

0.885 g/mL at 20 °C (lit.)

functional group

hydroxyl

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

Related Categories

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.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

10 - Combustible liquids

wgk_germany

WGK 2

flash_point_f

354.2 °F - closed cup

flash_point_c

179 °C - closed cup

ppe

Eyeshields, Gloves, type ABEK (EN14387) respirator filter

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Certificates of Analysis (COA)

Lot/Batch Number
WE382938/1
382938/1
342022/1

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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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