(E,E)-Farnesol

• CAS: 106-28-5
• Catalog Number: ACM106285-1
• Category: Alkanes
• Molecular Weight: 222.37
• Molecular Formula: C15H26O
• Synonyms: 2,6-Di-trans-farnesol
• IUPAC Name: (2E,6E)-3,7,11-Trimethyldodeca-2,6,10-trien-1-ol
• Canonical SMILES: CC(=CCCC(=CCCC(=CCO)C)C)C
• InChI: 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
• Boiling Point: 149 °C/4 mmHg(lit.)
• Melting Point: 61-63 °C
• Flash Point: 205 °F
• Density: 0.886 g/mL at 20 °C(lit.)
• Solubility: Insoluble in water
• Appearance: Slightly yellow to colourless liquid
• Storage: Sealed in dry, 2-8 °C
• Complexity: 265
• Exact Mass: 222.198365449
• Hazard Statements: Xi
• Isomeric SMILES: CC(=CCC/C(=C/CC/C(=C/CO)/C)/C)C
• Monoisotopic Mass: 222.198365449
• pKa: 14.42±0.10(Predicted)
• Refractive Index: n20/D 1.490(lit.)
• RIDADR: UN 3077 9 / PGIII
• Safety Description: 24/25-36/37
• Supplemental Hazard Statements: H317-H319
• Symbol: GHS07
• Topological Polar Surface Area: 20.2 Ų

Case Study

Study on the Potential Anti-inflammatory and Anticancer Properties of Farnesol

Jung, Young Yun, et al. Molecules, 2018, 23(11), 2827.

Farnesol is an acyclic sesquiterpene alcohol, which primarily present in the essential oils of various plants.
· Multiple Effects of Farnesol
Research indicates that farnesol possesses anti-cancer and anti-inflammatory properties, alleviating allergic asthma symptoms while diminishing gliosis and edema. This compound interacts with multiple tumorigenic proteins while controlling signal transduction pathways across different tumor cell lines. Through its bioactivity farnesol stimulates apoptotic processes while simultaneously obstructing cellular proliferation and angiogenesis as well as cellular survival mechanisms. Its anti-inflammatory and anti-cancer effects come from Ras protein modulation and nuclear factor kappa-light-chain-enhancer of activated B cells activation which results in decreased expression of inflammatory mediators including cyclooxygenase-2, inducible nitric oxide synthase, tumor necrosis factor-alpha, and interleukin-6.
· Frontier Research Cases
Breast Cancer: Research by Duncan and colleagues demonstrated that farnesol increases thyroid hormone receptor (THR) β1 expression and suppresses breast cancer cell line growth. MCF-7 breast cancer cell proliferation decreased while THRβ1 protein and mRNA levels increased when exposed to farnesol in a concentration and time-dependent manner.
Lung Cancer: Farnesol treatment caused ER stress in H460 lung cancer cells which activated the UPR and led to programmed cell death through the intrinsic pathway. The treatment led to elevated cleavage activity in caspase-9 and caspase-3 and poly (ADP-ribose) polymerase (PARP) but did not change caspase-8 levels.

Evaluation of the Potential of (E,E)-farnesol as a Vasodilator

Batista, Paulo Ricardo, et al. Chemico-Biological Interactions, 2023, 386, 110746.

This work investigated the vasodilatory effects of (E,E)-farnesol [(E,E)-FAR] in the human umbilical vein (HUV) of healthy donors to evaluate its therapeutic potential as a vasodilator.
Evaluation Methods
Ex vivo vascular reactivity assays were conducted using rings from isolated human umbilical veins (HUV), which were suspended in an organ bath to measure their isometric tension across various experimental conditions.
Evaluation Results
· (E,E)-FAR, at concentrations up to 1 mmol/L, does not alter the basal tone but induces vasorelaxation in HUV, exhibiting greater potency through electromechanical pathways.
· The primary mechanism for this vasorelaxant effect appears to be the inhibition of voltage-dependent Ca2+ channels, particularly L-type VOCC. In a Ca2+-free Krebs-Henseleit solution, (E,E)-FAR facilitates relaxation of contractions induced by depolarization and contractile agonists, likely due to decreased intracellular Ca2+ release, KATP channel activation, and/or ROCK pathway inactivation.
· Additionally, the involvement of K+ channels (BKCa, KATP, and KIR) contributes to the overall relaxation effect of (E,E)-FAR.
· Consequently, (E,E)-FAR shows considerable promise as a potential vasodilator for managing hypertensive conditions during pregnancy.

Custom Q&A

What is the molecular formula of (E,E)-Farnesol?

The molecular formula of (E,E)-Farnesol is C15H26O.

What is the molecular weight of (E,E)-Farnesol?

The molecular weight of (E,E)-Farnesol is 222.37 g/mol.

What is the IUPAC name of (E,E)-Farnesol?

The IUPAC name of (E,E)-Farnesol is (2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-ol.

What are some synonyms of (E,E)-Farnesol?

Some synonyms of (E,E)-Farnesol are farnesol, trans,trans-Farnesol, and 106-28-5.

What is the InChIKey of (E,E)-Farnesol?

The InChIKey of (E,E)-Farnesol is CRDAMVZIKSXKFV-YFVJMOTDSA-N.

What is the canonical SMILES of (E,E)-Farnesol?

The canonical SMILES of (E,E)-Farnesol is CC(=CCCC(=CCCC(=CCO)C)C)C.

What is the CAS number of (E,E)-Farnesol?

The CAS number of (E,E)-Farnesol is 4602-84-0.

What is the FEMA number of (E,E)-Farnesol?

The FEMA number of (E,E)-Farnesol is 2478.

What is the KEGG ID of (E,E)-Farnesol?

The KEGG ID of (E,E)-Farnesol is C01126.

What is the Wikipedia page of (E,E)-Farnesol?

The Wikipedia page of (E,E)-Farnesol is "Farnesol".