farnesol

Names

[ Name ]:
farnesol

[Synonym ]:
(2-trans,6-trans)-farnesol
(E,E)-3,7,11-Trimethyl-2,6,10-dodecatrien-1-ol
Stirrup-TPW
Stirrup-HB
(2E,6E)-3,7,11-Trimethyl-dodeca-2,6,10-trien-1-ol
trans,trans-3,7,11-Trimethyl-2,6,10-dodecatrien-1-ol
(2E,6E)-Farnesol
all-trans-farnesol
all-E-Farnesol
Farnesoi
EINECS 225-004-1
MFCD00002918
farnesyl bromide
2,6,10-Dodecatrien-1-ol, 3,7,11-trimethyl-, (E,E)-
(2E,6E)-3,7,11-Trimethyl-2,6,10-dodecatrien-1-ol
trans,trans-Farnesol
2,6,10-Dodecatrien-1-ol, 3,7,11-trimethyl-, (2E,6E)-
3,7,10-trimethyl-2,6,10-dodecatrien-1-ol
ALL TRANS FARNESOL
FARNESOLP
trans-Farnesol
Farnesol,(E,E)
3,7,11-Trimethyl-2,6,10-dodecatrienol
(E)-farnesol
farnesyl alcohol
(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-ol
3,7,11-Trimethyl-2,6,10-Dodecatrien-1-ol
E,E-farnesol
Stirrup-CRW
Polyprenol
Stirrup-H
Farnesol
(E,E)-Farnesol
3,7,11-Trimethyldodeca-2,6,10-trien-1-ol
3,7,11-Trimethyldodeca-2-trans,6-trans,10-trien-1-ol
fci119a
Inhibitor A2

Biological Activity

[Description]:

Farnesol is a sesquiterpene alcohol that modulates cell-to-cell communication in Candida albicans, and has the activity in inhibiting bacteria.

[Related Catalog]:

Signaling Pathways >> Anti-infection >> Bacterial

Research Areas >> Infection

Natural Products >> Terpenoids and Glycosides

[Target]

Human Endogenous Metabolite

[In Vitro]

Farnesol is a sesquiterpene alcohol that modulates cell-to-cell communication in Candida albicans. It is also shown that this molecule presents inhibitory effects against non-albicans Candida species, Paracoccidioides brasiliensis and bacteria. The minimum inhibitory concentrations (MICs) are determined in accordance with the M27-A3 protocol as described and Farnesol is tested at a concentration range of 0.29-150 μM. It is observed that Farnesol presents an inhibitory activity against C. neoformans and C. gattii (MIC range: 0.29-75.0 μM). Although Farnesol does not significantly alter phospholipase activity, a tendency to decrease this activity is observed[1].

[References]

[1]. Cordeiro Rde A, et al. Farnesol inhibits in vitro growth of the Cryptococcus neoformans species complex with no significant changes in virulence-related exoenzymes. Vet Microbiol. 2012 Oct 12;159(3-4):375-80.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
0.9±0.1 g/cm3

[ Boiling Point ]:
283.4±0.0 °C at 760 mmHg

[ Molecular Formula ]:
C₁₅H₂₆O

[ Molecular Weight ]:
222.366

[ Flash Point ]:
96.1±0.0 °C

[ Exact Mass ]:
222.198364

[ PSA ]:
20.23000

[ LogP ]:
5.31

[ Vapour Pressure ]:
0.0±1.3 mmHg at 25°C

[ Index of Refraction ]:
1.485

[ Storage condition ]:
−20°C

[ Stability ]:
Stable. Combustible. Incompatible with strong oxidizing agents.

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: JR4979000

CHEMICAL NAME :: 2,6,10-Dodecatrien-1-ol, 3,7,11-trimethyl-

CAS REGISTRY NUMBER :: 4602-84-0

LAST UPDATED :: 199712

DATA ITEMS CITED :: 6

MOLECULAR FORMULA :: C15-H26-O

MOLECULAR WEIGHT :: 222.41

WISWESSER LINE NOTATION :: Q2UY1&3UY1&3UY1&1

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 6 gm/kg

TOXIC EFFECTS :: Behavioral - somnolence (general depressed activity) Behavioral - antipsychotic

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 7400 mg/kg

TOXIC EFFECTS :: Behavioral - somnolence (general depressed activity) Behavioral - antipsychotic

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 443 mg/kg

TOXIC EFFECTS :: Behavioral - somnolence (general depressed activity) Behavioral - antipsychotic

MUTATION DATA

TYPE OF TEST :: DNA inhibition

TEST SYSTEM :: Insect - not otherwise specified Ovary

DOSE/DURATION :: 100 umol/L

REFERENCE :: ABCHA6 Agricultural and Biological Chemistry. (Maruzen Co. Ltd., POB 5050, Tokyo International, Tokyo 100-31, Japan) V.25- 1961- Volume(issue)/page/year: 43,1285,1979 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - X5190 No. of Facilities: 7 (estimated) No. of Industries: 1 No. of Occupations: 5 No. of Employees: 1557 (estimated) No. of Female Employees: 276 (estimated)

Safety Information

[ Symbol ]:

GHS07, GHS09

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H315-H317-H319-H411

[ Precautionary Statements ]:
P273-P280-P333 + P313-P337 + P313-P391-P501

[ Personal Protective Equipment ]:
Eyeshields;Gloves;half-mask respirator (US);multi-purpose combination respirator cartridge (US)

[ Hazard Codes ]:
Xi: Irritant;

[ Risk Phrases ]:
R24/25

[ Safety Phrases ]:
S22-S24/25

[ RIDADR ]:
UN 3082 9 / PGIII

[ WGK Germany ]:
3

[ RTECS ]:
JR4979000

[ HS Code ]:
2905290000

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2905290000

[ Summary ]:
2905290000 unsaturated monohydric alcohols。Supervision conditions:None。VAT:17.0%。Tax rebate rate:9.0%。MFN tariff:5.5%。General tariff:30.0%

Articles

Developmentally regulated sesquiterpene production confers resistance to Colletotrichum gloeosporioides in ripe pepper fruits.

PLoS ONE 9(10) , e109453, (2014)

Sesquiterpenoid capsidiol, exhibiting antifungal activity against pathogenic fungus, is accumulated in infected ripe pepper fruits. In this study, we found a negative relation between the capsidiol le...

Farnesol induces apoptosis-like cell death in the pathogenic fungus Aspergillus flavus.

Mycologia 106(5) , 881-8, (2014)

Farnesol (FOH) is known to induce apoptosis in some fungi and mammalian cells. We treated Aspergillus flavus, one of the leading causes of human invasive aspergillosis and a key producer of the most p...

Pluronics-Formulated Farnesol Promotes Efficient Killing and Demonstrates Novel Interactions with Streptococcus mutans Biofilms.

PLoS ONE 10 , e0133886, (2015)

Streptococcus mutans is the primary causative agent of dental caries, one of the most prevalent diseases in the United States. Previously published studies have shown that Pluronic-based tooth-binding...