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W247804

Sigma-Aldrich

Farnesol

mixture of isomers, ≥95%, stabilized, FG

Synonym(s):

3,7,11-Trimethyl-2,6,10-dodecatrien-1-ol

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About This Item

Linear Formula:
(CH3)2C=CHCH2CH2C(CH3)=CHCH2CH2C(CH3)=CHCH2OH
CAS Number:
4602-84-0
Molecular Weight:
222.37
FEMA Number:
2478
Beilstein:
1763926
EC Number:
225-004-1
Council of Europe no.:
78
MDL number:
MFCD00002918
UNSPSC Code:
12164502
PubChem Substance ID:
24901122
Flavis number:
2.029
NACRES:
NA.21

biological source

synthetic

Quality Level

400

grade

FG
Halal
Kosher

reg. compliance

EU Regulation 1334/2008 & 178/2002
FDA 21 CFR 117
FDA 21 CFR 172.515

Assay

≥95%

contains

α-tocopherol (synthetic stabilizer)

may contain

≤50 ppm hexane

refractive index

n20/D 1.489 (lit.)

bp

149 °C/4 mmHg (lit.)

density

0.886 g/mL at 20 °C (lit.)

application(s)

flavors and fragrances

Documentation

see Safety & Documentation for available documents

food allergen

no known allergens

Organoleptic

fresh; floral; sweet

SMILES string

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

InChI

1S/C15H26O/c1-13(2)7-5-8-14(3)9-6-10-15(4)11-12-16/h7,9,11,16H,5-6,8,10,12H2,1-4H3/b14-9+,15-11+

InChI key

CRDAMVZIKSXKFV-YFVJMOTDSA-N

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Application


  • Farnesol repurposing for prevention and treatment of Acinetobacter baumannii biofilms.: This article explores the efficacy of repurposing farnesol for preventing and treating biofilms caused by Acinetobacter baumannii, highlighting its potential as an antibacterial agent (Tan et al., 2024).

  • Methyl-Jasmonate Functions as a Molecular Switch Promoting Cross-Talk between Pathways for the Biosynthesis of Isoprenoid Backbones Used to Modify Proteins in Plants.: This study investigates the role of methyl-jasmonate in regulating the biosynthesis of isoprenoid backbones, which are crucial for post-translational modification of proteins in plants and may involve farnesol as an intermediate or by-product (Chevalier et al., 2024).

  • Repurposing Farnesol for Combating Drug-Resistant and Persistent Single and Polymicrobial Biofilms.: This article discusses the potential of repurposing farnesol to combat drug-resistant and persistent biofilms, demonstrating its utility in enhancing antibiotic efficacy and addressing antimicrobial resistance (Tan et al., 2024).

Biochem/physiol Actions

Taste at 10 ppm

Other Notes

Natural occurrence: Apricot, orange peel and oil, grapefruit juice, cloves, ginger thyme beef, whiskey basil, papaya, anise seed and balsam of Peru.

Pictograms

Exclamation markEnvironment
GHS07,GHS09

Signal Word

Warning

Hazard Statements

H315,H317,H410

Hazard Classifications

Aquatic Acute 1 - Aquatic Chronic 1 - Skin Irrit. 2 - Skin Sens. 1

Storage Class Code

10 - Combustible liquids

WGK

WGK 2

Flash Point(F)

311.0 °F - closed cup

Flash Point(C)

155 °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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Phillip A Lichtor et al.
Nature chemistry, 4(12), 990-995 (2012-11-24)
Selectivity in the catalytic functionalization of complex molecules is a major challenge in chemical synthesis. The problem is magnified when there are several possible stereochemical outcomes and when similar functional groups occur repeatedly within the same molecule. Selective polyene oxidation
N Charette et al.
Cell death & disease, 4, e471-e471 (2013-01-26)
Ras activation is a frequent event in human hepatocarcinoma that may contribute to resistance towards apoptosis. Salirasib is a ras and mTOR inhibitor that induces a pro-apoptotic phenotype in human hepatocarcinoma cell lines. In this work, we evaluate whether salirasib
Rossana de Aguiar Cordeiro et al.
Veterinary microbiology, 159(3-4), 375-380 (2012-05-15)
Farnesol is a sesquiterpene alcohol that modulates cell-to-cell communication in Candida albicans. In recent years, several studies have shown that this molecule presents inhibitory effects against non-albicans Candida species, Paracoccidioides brasiliensis and bacteria. The present study aimed at determining the
Najla Nasr et al.
Blood, 120(4), 778-788 (2012-06-09)
Macrophages are key target cells for HIV-1. HIV-1(BaL) induced a subset of interferon-stimulated genes in monocyte-derived macrophages (MDMs), which differed from that in monocyte-derived dendritic cells and CD4 T cells, without inducing any interferons. Inhibition of type I interferon induction
Joung Hyuck Joo et al.
Cancer letters, 287(2), 123-135 (2009-06-13)
The isoprenoid alcohol farnesol is an effective inducer of cell cycle arrest and apoptosis in a variety of carcinoma cell types. In addition, farnesol has been reported to inhibit tumorigenesis in several animal models suggesting that it functions as a
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