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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

Quality Level

100

Assay

≥90% (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

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

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Geranyllinalool (Diterpene Alcohol).
Lemaire M, et al.
Journal of Chemical Ecology, 16(6), 2067-2079 (1990)
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
Sol A Green et al.
Journal of experimental botany, 63(5), 1951-1967 (2011-12-14)
Flowers of the kiwifruit species Actinidia chinensis produce a mixture of sesquiterpenes derived from farnesyl diphosphate (FDP) and monoterpenes derived from geranyl diphosphate (GDP). The tertiary sesquiterpene alcohol (E)-nerolidol was the major emitted volatile detected by headspace analysis. Contrastingly, in
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)
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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