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277541

Sigma-Aldrich

trans,trans-Farnesol

96%

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
Beilstein:
1723039
MDL number:
MFCD00002918
UNSPSC Code:
12352100
PubChem Substance ID:
24856767
NACRES:
NA.22

Quality Level

200

Assay

96%

form

liquid

refractive index

n20/D 1.490 (lit.)

bp

137 °C/3 mmHg (lit.)

density

0.879 g/mL at 25 °C (lit.)

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

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General description

trans,trans-Farnesol is sesquiterpene alcohol, which is commonly found in many essential oils, citrus fruits, propolis, and plant-derived foods and beverages. It is an effective bioactive agent that can be used in pharmaceuticals and cosmetics.

Application

trans,trans-Farnesol has been used in the synthesis of:
  • Cecropia juvenile hormone
  • terpenes, such as squalenes, cembranoids and forskolin

Other Notes

A sesquiterpene alcohol found in many essential oils.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H317

Hazard Classifications

Skin Sens. 1

WGK

WGK 3

Flash Point(F)

closed cup

Flash Point(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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Tetrahedron Letters, 34, 1721-1721 (1993)
Influences of trans-trans farnesol, a membrane-targeting sesquiterpenoid, on Streptococcus mutans physiology and survival within mixed-species oral biofilms
Jeon J-G, et al.
International Journal of Oral Science, 3, 98-106 (2011)
Assessment of the antioxidant and antiproliferative effects of sesquiterpenic compounds in in vitro Caco-2 cell models
Vinholes Juliana, et al.
Food Chemistry, 156, 204-211 (2014)
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)
The Journal of Organic Chemistry, 59, 5803-5803 (1994)
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