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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/REAXYS Number:
1726098
EC Number:
Z-7541493
MDL number:
MFCD00002919
UNSPSC Code:
12352100
PubChem Substance ID:
24848440
NACRES:
NA.22

Quality Level

100

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.)

functional group

hydroxyl

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

signalword

Warning

hcodes

H315,H413

Hazard Classifications

Aquatic Chronic 4 - Skin Irrit. 2

Storage Class

10 - Combustible liquids

wgk_germany

WGK 2

flash_point_f

368.6 °F

flash_point_c

187 °C

ppe

Eyeshields, Gloves, type ABEK (EN14387) respirator filter

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Certificates of Analysis (COA)

Lot/Batch Number
SHBL6818
SHBL6817
MKBX5304V
MKBX6255V
MKBP8916V

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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
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
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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