Phytol

HCID 5280435

Basic information

CAS
150-86-7
Standard SMILES
C/C(=C\CO)CCC[C@H](C)CCC[C@H](C)CCCC(C)C
InChIKey
BOTWFXYSPFMFNR-PYDDKJGSSA-N
Molecular formula
C20H40O
Average molar mass
296.5 g/mol
Monoisotopic mass
296.3079159

Overview

Phytol is a diterpenoid that is hexadec-2-en-1-ol substituted by methyl groups at positions 3, 7, 11 and 15. It has a role as a schistosomicide drug, a plant metabolite and an algal metabolite. It is a diterpenoid and a long-chain primary fatty alcohol.

Names & identifiers

Preferred name
Phytol
IUPAC
(E,7R,11R)-3,7,11,15-tetramethylhexadec-2-en-1-ol
English name
Phytol
Molecular formula
C20H40O
Molecular weight
296.53

Names & synonyms

Phytol150-86-7trans-Phytol(E,7R,11R)-3,7,11,15-tetramethylhexadec-2-en-1-ol(2E,7R,11R)-3,7,11,15-tetramethyl-2-hexadecen-1-olMZQ4XE15TPCHEBI:17327DTXSID1040586PHYTOL, (E)-3R,7R,11R,15-tetramethyl-2E-hexadecen-1-olFEMA NO. 4196, E-2-Hexadecen-1-ol, 3,7,11,15-tetramethyl-, (7R,11R)-
Show more names
3,7,11,15-TETRAMETHYL-2-HEXADECEN-1-OL(7R,11R,E)-3,7,11,15-Tetramethylhexadec-2-en-1-olNatural PhytolPhytol, 90.0%(GC)2-Hexadecen-1-ol, 3,7,11,15-tetramethyl-, [R-[R*,R*-(E)]]-Phytol>Aids058679(E)-phytol
RefChem:6139DTXCID9020586205-776-6123164-54-52-Hexadecen-1-ol, 3,7,11,15-tetramethyl-, (R-(R*,R*))-5BC2RZ81NGFEMA No. 4196Phytol, (E,Z)-

Database identifiers

CAS
150-86-7
PubChem CID
5280435
DTXSID
DTXSID1040586
ChEMBL
CHEMBL1644111、CHEMBL3039479
ChEBI
CHEBI:17327
UNII
MZQ4XE15TP
EC Number
205-776-6、416-120-5
Nikkaji
J6.120D

Properties

Computed structural properties

XLogP
8.2
Topological polar surface area
20.2 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
1
Rotatable bonds
13
Heavy atoms
21

Experimental & physicochemical properties

LipidsLipids -> Prenol Lipids [PR] -> Isoprenoids [PR01] -> C20 isoprenoids (diterpenes) [PR0104]
FragrancesFragrance Ingredient (Phytol) -> IFRA transparency List
Food AdditivesFLAVORING AGENT OR ADJUVANT -> FDA Substance added to food
Density0.847-0.863
Flavoring AgentsEU Flavoring substances
Solubility · 3 items

very slightly

Practically insoluble to insoluble in water

Soluble (in ethanol)

Physicochemical properties

Melting point
25 °C · <25 °C
Boiling point
202 · 202-204 °C (10 mmHg)
Density
0.85 · 0.85
refractive index
1.461 · 1.461-1.469
FEMA
4196 · 4196 | PHYTOL
FLAVIS Number
2.204 · 02.204 | Phytol

Safety & regulation

GHS classification

GHS Classification · 6 items

This chemical does not meet GHS hazard criteria for < 0.1% (1 of 1540) of reports.

Warning

H315 (> 99.9%): Causes skin irritation [Warning Skin corrosion/irritation]

P264, P273, P280, P302+P352, P321, P332+P317, P362+P364, P391, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 1540 reports by companies from 10 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Warning

Hazard information

Regulatory Information · 4 items

Chemical: 2-Hexadecen-1-ol, 3,7,11,15-tetramethyl-, [R-[R*,R*-(E)]]-

Commission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)

Status: Active Update: 12-05-2017 https://echa.europa.eu/registration-dossier/-/registered-dossier/19523

Phytol: Does not have an individual approval but may be used under an appropriate group standard

Hazard Classes and Categories · 2 items

Skin Irrit. 2 (> 99.9%)

Skin Irrit. 2 (100%)

Safety data

tsca
TSCA listed
rtecs
TJ3490000
hs_code
29052290
Toxicity
rabbit,LD50,skin,> 5gm/kg (5000mg/kg),Food and Chemical Toxicology. Vol. 20, Pg. 811, 1982.
risk_code
36/37/38
Signal word
Danger

Chemistry & industry

Pharmacology

Tissue LocationsFibroblasts
Cellular LocationsExtracellular

Uses & manufacturing

Household ProductsInformation on 3 consumer products that contain Phytol in the following categories is provided:
Use Classification · 3 items

Fragrance Ingredients

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

Flavoring Agents -> JECFA Flavorings Index

General Manufacturing Information2-Hexadecen-1-ol, 3,7,11,15-tetramethyl-, (2E,7R,11R)-: ACTIVE
Applications · 3 items

DescriptionPhytol is a diterpene alcohol obtained from the degradation of chlorophyll and has been used in the synthesis of Vitamins E and K. During the digestion process of ruminants, phytol is liberated from chlorophyll and converted to phytanic acid to be stored in fats. While humans cannot derive phytol from chlorophyll, free phytol, obtained from the consumption of ruminant adipose tissue and dairy products, is readily absorbed in the small intestine and converted to phytanic acid. Phytanic acid accumulates to toxic levels in a number of metabolic disorders, and the conversion of phytol to phytanic acid has been shown to be regulated via the activation of peroxisome proliferator-activated receptor α (PPARα). Phytol and its metabolites have also been reported to activate retinoid X receptors (RXRs; Kis range from 2.3-67.2 μM) and to promote the activity of PPAR/RXR heterodimers. Phytol also demonstrates sedative and anxiolytic effects through interaction with the GABAA receptor, and it has been explored as an antischistosomal agent in a mouse model of schistosomiasis.

OccurrenceReported found in Herniaria incana lam oil Greece (2.60%) and Witch hazel leaf oil (9.79%).

Usestrans-Phytol is a reagent that is used in the preparation of α-tocopherol analogs as mitochondrial antioxidants. It is also used as a precursor for the manufacture of synthetic forms of vitamin E and vitamin K1.

Upstream & downstream products

Downstream products

Suppliers100 total

梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
Shandong chuangyingchemical Co., Ltd.18853181302 · [email protected]
河北创海生物科技有限公司+86-86-13131129325 · [email protected]
陕西帕尼尔生物科技有限公司029-84385017; +8613259417953 · [email protected]
北京安司莫森技术有限公司010-82954736 13391601435 · [email protected]
Additional notes · 1 item

DefinitionChEBI: Phytol is a diterpenoid that is hexadec-2-en-1-ol substituted by methyl groups at positions 3, 7, 11 and 15. It has a role as a plant metabolite, a schistosomicide drug and an algal metabolite. It is a diterpenoid and a long-chain primary fatty alcohol.

Related reactions

51 records

Compound notes

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