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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:
6713421
EC Number:
214-201-8
MDL number:
MFCD00059363
UNSPSC Code:
12352100
PubChem Substance ID:
329757417
NACRES:
NA.22

grade

technical

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

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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

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

10 - Combustible liquids

WGK

WGK 2

Flash Point(F)

354.2 °F - closed cup

Flash Point(C)

179 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

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

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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)
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.
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
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
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