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Merck
CN

46193

trans,trans-Farnesol

purum, ≥95.0% (GC)

Synonym(s):

(E,E)-3,7,11-Trimethyl-2,6,10-dodecatrien-1-ol, trans,trans-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:
106-28-5
Molecular Weight:
222.37
PubChem Substance ID:
24869919
UNSPSC Code:
12352100
Beilstein/REAXYS Number:
1723039
MDL number:
MFCD00002918

Key Documents

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SMILES string

C\C(C)=C\CC\C(C)=C\CC\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

grade

purum

assay

≥95.0% (GC)

bp

137 °C/3 mmHg (lit.)

density

0.879 g/mL at 25 °C (lit.)

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Other Notes

A sesquiterpene alcohol found in many essential oils.

pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H317

Hazard Classifications

Skin Sens. 1

Storage Class

10 - Combustible liquids

wgk

WGK 3

flash_point_f

204.8 °F - closed cup

flash_point_c

96.00 °C - closed cup

ppe

Eyeshields, Gloves

Regulatory Information

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Jae-Gyu Jeon et al.
International journal of oral science, 3(2), 98-106 (2011-04-13)
Trans-trans farnesol (tt-farnesol) is a bioactive sesquiterpene alcohol commonly found in propolis (a beehive product) and citrus fruits, which disrupts the ability of Streptococcus mutans (S. mutans) to form virulent biofilms. In this study, we investigated whether tt-farnesol affects cell-membrane
K H Overton et al.
The Biochemical journal, 144(3), 585-592 (1974-12-01)
A cell-free system obtained from tissue cultures of Andrographis paniculata produces 2-trans,6-trans-farnesol (trans,trans-farnesol) and 2-cis,6-trans-farnesol (cis,trans-farnesol) (5:1), incorporating 10% of the radioactivity from 3R-[2-(14)C]mevalonate. There is total loss of (3)H from 3RS-[2-(14)C,(4S)-4-(3)H(1)]mevalonate and total retention from the (4R) isomer in
Interconversion of trans, trans and cis, trans farnesol by enzymes from Andrographis.
Overton KH and Roberts FM.
Phytochemistry, 13(12), 2741-2743 (1974)
Synthesis of cecropia juvenile hormone from trans,trans-farnesol.
E E van Tamelen et al.
Journal of the American Chemical Society, 92(3), 737-738 (1970-02-11)
Tristan Rossignol et al.
Antimicrobial agents and chemotherapy, 51(7), 2304-2312 (2007-08-09)
In Candida albicans, the quorum-sensing molecule farnesol inhibits the transition from yeast to hyphae but has no effect on cellular growth. We show that the addition of exogenous farnesol to cultures of Candida parapsilosis causes the cells to arrest, but
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