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139912

Sigma-Aldrich

Phytol

95%, mixture of isomers

Synonym(s):

3,7,11,15-Tetramethyl-2-hexadecen-1-ol

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About This Item

Linear Formula:
CH3[CH(CH3)(CH2)3]3C(CH3)=CHCH2OH
CAS Number:
7541-49-3
Molecular Weight:
296.53
Beilstein:
1726098
EC Number:
Z-7541493
MDL number:
MFCD00002919
UNSPSC Code:
12352100
PubChem Substance ID:
24848440
NACRES:
NA.22

Assay

95%

form

(Liquid or Viscous Liquid)

refractive index

n20/D 1.463 (lit.)

bp

202-204 °C/10 mmHg (lit.)

density

0.85 g/mL at 25 °C (lit.)

SMILES string

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

InChI

1S/C20H40O/c1-17(2)9-6-10-18(3)11-7-12-19(4)13-8-14-20(5)15-16-21/h15,17-19,21H,6-14,16H2,1-5H3/b20-15+

InChI key

BOTWFXYSPFMFNR-HMMYKYKNSA-N

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General description

Phytol is a diterpene alcohol and is widely used as a food additive and in medicinal field. It undergoes Mitsunobu reaction with 5-fluorouridine to yield the nucleoterpenes.

Application

Phytol was used to investigate the electroantennogram response of males and females of the potato tuber moth, Phthorimaea operculella to various plant volatiles. It was used in the synthesis of pristanic acid (2,6,10,14-tetramethylpentadecanoic acid).

Biochem/physiol Actions

Phytol exhibits potential anti-Schistosomal properties. It induces sedative and anxiolytic-like effects in mice.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H413

Precautionary Statements

P273 - P302 + P352

Hazard Classifications

Aquatic Chronic 4 - Skin Irrit. 2

Storage Class Code

10 - Combustible liquids

WGK

WGK 2

Flash Point(F)

368.6 °F

Flash Point(C)

187 °C

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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P D Das et al.
Journal of biosciences, 32(2), 339-349 (2007-04-17)
Electroantennograms (EAGs)were recorded from males and females of the potato tuber moth,Phthorimaea operculella in response to a broad range of plant volatile compounds belonging to diverse chemical classes.The responses to 27 compounds were evaluated,which indicated significant differences in EAGs between
Jéssica Pereira Costa et al.
Brain research, 1547, 34-42 (2013-12-18)
Phytol, a branched chain unsaturated alcohol, is particularly interesting because it is an isolated compound from essential oils of different medicinal plants. The aim of this study was to evaluate the anxiolytic-like effects of phytol in animal models to clarify
P P Van Veldhoven et al.
The Journal of biological chemistry, 266(36), 24676-24683 (1991-12-25)
Isoprenoid (branched) fatty acids such as pristanic acid can be degraded via beta-oxidation in peroxisomes. We synthesized 2-methylpalmitoyl-CoA as a model substrate in order to study the first step of the peroxisomal beta-oxidation of branched fatty acids, catalyzed by an
Edith Malecki et al.
Chemistry & biodiversity, 10(12), 2209-2220 (2013-12-12)
The cancerostatic 5-fluorouridine (5-FUrd; 1) was sequentially sugar-protected by introduction of a 2',3'-O-heptylidene ketal group (→2), followed by 5'-O-monomethoxytritylation (→3). This fully protected derivative was submitted to Mitsunobu reactions with either phytol ((Z and E)-isomer) or nerol ((Z)-isomer) to yield
Josué de Moraes et al.
PLoS neglected tropical diseases, 8(1), e2617-e2617 (2014-01-07)
Schistosomiasis is a major endemic disease that affects hundreds of millions worldwide. Since the treatment and control of this parasitic disease rely on a single drug, praziquantel, it is imperative that new effective drugs are developed. Here, we report that
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