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
Show more names
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
- Formal charge
- 0
- Complexity
- 255
Experimental & physicochemical properties
Solubility
very slightly
Practically insoluble to insoluble in water
Soluble (in ethanol)
Boiling Point
202.00 to 204.00 °C. @ 10.00 mm Hg
131-132 °C (0.1 mm Hg)
Physical Description
Solid
Colourless to yellow viscous liquid; Faint floral aroma
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
- Flash point
- 179 ℃ · 179℃ (Cleveland open test)
- storage temp.
- 2 · Inert atmosphere,2-8°C
- solubility
- Insoluble in water, miscible with alcohol and oils
- pka
- 14.45 · 14.45±0.10(Predicted)
- form
- Oil
- color
- Light Yellow to Yellow
- Odor
- 100 % · at 100.00 %. delicate floral balsam powdery waxy
- Odor Type
- floral
- Merck
- 14 · 14,7390
- JECFA Number
- 1832 · 1832
- Henry's Law Constant
- 1 · 1.0×10-2 mol/(m3Pa) at 25℃, Ebert et al. (2023)
- Stability
- Light Sensitive
- Cosmetics Ingredients Functions
- SKIN CONDITIONING - EMOLLIENTPERFUMINGFRAGRANCE
- InChIKey
- BOTWFXYSPFMFNR-PFIWFTBQSA-N
- LogP
- 8.23 · 8.23
- CAS DataBase Reference
- 150 · 150-86-7(CAS DataBase Reference)
- Substances Added to Food (formerly EAFUS)
- PHYTOL
- EWG's Food Scores
- 1 · 1
- NCI Dictionary of Cancer Terms
- phytol
- FDA UNII
- 4 XE15TP · MZQ4XE15TP
- EPA Substance Registry System
- Phytol (150-86-7)
- Symbol(GHS)
- 5 · GHS05,GHS07,GHS08,GHS09
- Signal word
- Danger
- Hazard statements
- 302 · H302-H318-H360-H370-H372-H317-H411
- Precautionary statements
- 501 · P501-P273-P272-P260-P270-P202-P201-P264-P280-P302+P352-P391-P308+P311-P362+P364-P333+P313-P301+P312+P330-P305+P351+P338+P310-P405
- Hazard Codes
- Xi
- Risk Statements
- 36 · 36/37/38
- Safety Statements
- 37 · 37/39-26-36
- RTECS
- 3490000 · TJ3490000
- TSCA
- TSCA listed
- HS Code
- 29052290 · 29052290
- Toxicity
- 50 · rabbit,LD50,skin,> 5gm/kg (5000mg/kg),Food and Chemical Toxicology. Vol. 20, Pg. 811, 1982.
- REACH Registrations
- Active
Safety & regulation
GHS classification
GHS Classification
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
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
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
- Symbol(GHS)
- GHS05,GHS07,GHS08,GHS09
- hazard_code
- Xi
- safety_code
- 37/39-26-36
- Hazard statements
- H302-H318-H360-H370-H372-H317-H411
- REACH Registrations
- Active
- Precautionary statements
- P501-P273-P272-P260-P270-P202-P201-P264-P280-P302+P352-P391-P308+P311-P362+P364-P333+P313-P301+P312+P330-P305+P351+P338+P310-P405
Chemistry & industry
Pharmacology
Uses & manufacturing
Use Classification
Fragrance Ingredients
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
Flavoring Agents -> JECFA Flavorings Index
Applications
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
Additional notes
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
Compound notes
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