SlideShare utilise les cookies pour améliorer les fonctionnalités et les performances, et également pour vous montrer des publicités pertinentes. Si vous continuez à naviguer sur ce site, vous acceptez l’utilisation de cookies. Consultez nos Conditions d’utilisation et notre Politique de confidentialité.
SlideShare utilise les cookies pour améliorer les fonctionnalités et les performances, et également pour vous montrer des publicités pertinentes. Si vous continuez à naviguer sur ce site, vous acceptez l’utilisation de cookies. Consultez notre Politique de confidentialité et nos Conditions d’utilisation pour en savoir plus.
Safrole is a phenylpropene. It is a colorless or slightly
yellow oily liquid typically extracted from the root-bark or
the fruit of sassafras plants in the form of sassafras oil, or is
synthesized from catechol or other related methylenedioxy
Safrole is a member of the BENZODIOXOLES that is a
constituent of several VOLATILE OILS, notably SASSAFRAS
oil. It is a precursor in the synthesis of the insecticide
PIPERONYL BUTOXIDE and the drug N-methyl-3,4-
Property Name Property Value
Molecular Weight 162.188 g/mol
Canonical SMILES C=CCC1=CC2=C(C=C1)OCO2
IUPAC Name 5-prop-2-enyl-1,3-benzodioxole
Hydrogen Bond Donor Count 0
Hydrogen Bond Acceptor Count 2
Rotatable Bond Count 2
Topological Polar Surface Area 18.5 A^2
Monoisotopic Mass 162.068 g/mol
Exact Mass 162.068 g/mol
Molecular Formula C10H10O2
Clear colorless or slightly yellow liquid.
Denser than water (density 1.09 g / cm3) and insoluble
Hence sinks in water.
Obtained from oil of sassafras or oil of camphor.
prisms, or crystals.
Boiling Point 232–234 °C.
Melting Point 11.2 °C.
Solubility Miscible with chloroform, ether, Soluble in
alcohol; slightly soluble in propylene glycol; insoluble
in water, glycerol
Decomposition : When heated to decomposition it emits
acrid smoke and irritating fumes.
Methods of Manufacturing
Distillation of essential oils rich in /safrole/
An uneconomical synthesis starts with catechol methylene ether reacted with allyl
chloride; also 4-allyl alcohol with methylene iodide.
In addition to safrole, oil of sassafras contains small amounts of eugenol, pinene,
phellandrene, sesquiterpene and d-camphor.
These are potential impurities in technical safrole.
Steam distillation of dried root bark
produces an essential oil consisting
mostly of safrole that once was
extensively used as a fragrance in
perfumes and soaps, food and for
aromatherapy. The yield of this oil from
American sassafram is quite low and
great effort is needed to produce useful
amounts of the root bark. Commecial
"sassafras oil" generally is a by product
of camphor production in Asia or comes
from related trees in Brazil. Safrole is a
precursor for the clandestine
manufacture of the drug ecstacy, and as
such, its transport is monitored
Safrole can be synthesized in three steps from unwatched chemicals in good yield:
EXPERIMENTAL PROCEDURE :
In a 2L-round bottom flask with two neck adapter (reflux condenser, dropping funnel)
immersed in an oil bath / magnetic stirrer, are placed 95 mL (1.36 moles) of
dibromomethane, 180 mL water and 4-5 mL trioctylmethylammonium chloride (PTC,
"Adogen 464, Aliquat 336"). On the top of the reflux condenser, a tube is drawn to a gas
washing bottle to give some protection against the atmosphere.) The contents of the
flask are heated and stirred to reflux and a previous made solution of 100 g (0.91 moles)
1,2-dihydroxybenzene (catechol), 91 g sodium hydroxide (2.275 moles) and 450 mL
water is added to the flask (the contents are stirred vigorously and refluxed
continously). The addition time is 120 min, thereafter the contents are stirred and
refluxed 90 min. The product is distilled with steam (add water continously to flask,
distill off water and product). After 1.5 liters of distillate are collected, the distillate is
saturated with table salt, and extracted three times with ether (better: tert-butyl methyl
ether, non watched, and not so dangerous). The etheral extracts are dried with sodium
sulfate, the whole is filtered, and the drying agent washed with 2x30 mL of solvent. The
combined filtrates are evaporated (rotavap), and the residue is distilled in vacuum. At
60-80°C (20 mmHg), 87 g 1,2-methylenedioxybenzene distills, containing about 8% of
unreacted dibromomethane. The gum in the reaction/distillation flasks is removed with
In a 500 mL-round bottom flask with reflux condenser (situated in an oil bath and
with magnetic stirrer) are placed 70 g of the product from step 1 (92% pure 1,2-
methylenedioxybenzene, 0.53 moles), 100 g N-bromosuccinimide and 260 mL
chloroform (dry). After three hours of refluxing and stirring, the solution is cooled
to room temp, and the the succinimide is filtered off with suction, and washed
2x20 mL of chloroform. The combined filtrates are evaporated, and the residue is
vacuum distilled. At 125-135°C (40 mmHg), a mixture of product and succinimide
distills, which is diluted with twice the volume of diethyl ether, stored 3 hrs. over
solid sodium hydroxide and washed thoroughly with water. After thorough drying
over sodium sulfate, the drying agent is filtered off and washed with 20 mL
ether. The ether is evaporated (rotavap), the yellow-brownish residual oil is
sufficiently pure for the next step (the refractive index at 25°C is 1.583). The yield
72 g, 67% of theory calculated to pure 1,2-methylenedioxybenzene being used.
In a 500 mL flask (immersed in a magnetic stirrer / oil bath) are placed 10-11g
magnesium turnings, and 150 mL tetrahydrofuran (freshly distilled from sodium). After
the addition of a little iodine crystal and 2 mL dibromomethane to start the Grignard
reaction, the 72 g of 4-bromo-1,2-methylenedioxybenzene (step 2) are added to
maintain gently reflux. To start up, heating of the bath to 50°C is recommended. After
the addition, which takes about 60 min., the whole is stirred and refluxed 1 hr., and the
brown liquid is rapidly decanted to a very dry 500 mL flask with dropping funnel and
reflux condenser. The magnesium turnings are washed with additional 20 mL dry THF,
the washing is added to the Grignard solution. A little (0.5 g) copper(I)iodide is added,
and with cooling in an ice-bath, 40 mL (0.47 moles) allyl bromide are added dropwise,
the internal temperature should not exceed 40°C. After standing overnight, followed
1 hr of refluxing, the reaction mixture is suspended in a solution of 20 mL 37%
hydrochloric acid in 500 mL water and this is added to 80 mL 25% ammonia, and the
solution is steam distilled as above. After collecting 2 L distillate, the distillate is
to congo red (pH 4) with hydrochloric acid, saturated with table salt, and extracted
4x200 mL ether. The combined extracts are dried with sodium hydroxide, evaporated
(rotavap), and the residue taken up in ether, and washed thorougly with sodium
hydroxide. After drying (sodium sulfate), the drying agent is filtered, washed with 20
ether, and the combined extracts are evaporated. The residue is vacuum distilled, 39 g
(67% of theory) of safrole, boiling at 120-130°C (20-25 mmHg), are obtained.
and typically smelling oil. Total yield (from the catechol), 32-33% of theory.
Safrole oil has been used as an antiseptic for many centuries. It is an antimicrobial
extract. Safrole oil contains many antibacterial, antifungal and antiviral properties.
has thus been slated to be an effective antiseptic. Its antifungal properties also
make it a great fungicide.
Safrole is an effective agent that combats dandruff and lice. A few drops of oil in
the water that you use to wash your hair will go a long way in improving your
health. Also, its natural moisture trapping tendency helps soften the hair.
Safrole oil has many uses for the skin. Its natural emollient characteristics help
get supple skin, while it’s many antimicrobial properties help cure ailments like
acne, boils, ringworm and minor cuts and bruises. Safrole oil can also be used to
relieve pain from insect bites.
APPLICATIONS of safrole oıl
Safrole essential oil was initially used as a perfume. It has also been used widely
aromatherapy. It has a unique calming aroma. The ancient world used safrole for
soaps and perfumes. It is still used as a popular essential oil, with a distinct
We know that safrole oil treats acne and other skin ailments. It achieves this by
fortifying the liver. The liver’s processes flush excess toxins from the system.
oil fortifies the liver and thus helps cure acne, eczema and even psoriasis.
Safrole oil works as a great cleanser. It can be used to clean and polish the floors,
surfaces and pretty much anything. Safrole mixes with the other chemicals to give
your cleaning solution a uniquely pleasant aroma. Thus, you can use copious
amounts of Safrole to keep your floor clean.
Side Effects Of Safrole Oil:
Although safrole oil has many benefits, there are some side effects that you
be aware of:
Apart from being a known carcinogen, excess amounts of safrole oil can induce
nausea, drowsiness and hallucinations.
Pregnant women should refrain from using safrole as it may cause complications
FDA has banned the use of Safrole.
It can no longer be used for flavoring food and as an additive because of its
Patent ID Patent Title
Pesticidally active bicyclic heterocycles with
sulphur containing substituents
Compositions and methods for combination
Compounds and methods for preventing or
treating sensory hair cell death
Topical skin care formulations comprising plant
US2016278408 Organic Compounds 2013-10-02 2016-09-29
CARBON FIBRE COMPOSITIONS COMPRISING
US2016271025 ABRASIVE CLEANING COMPOSITION 2014-12-12 2016-09-22
US2016271033 SKIN RENEWAL ENHANCER 2016-03-21 2016-09-22
COMPOUNDS AND FORMS OF TREATMENT FOR
FEMALE SEXUAL DISORDERS
US2016271209 ANTIBACTERIAL COMPOSITION 2013-11-08 2016-09-22
The National Institute for Occupational Safety and Health – NIOSH
European Chemicals Agency – ECHA 5-allyl-1,3-benzodioxole
EU REGULATION (EC) No 1272/2008 safrole;5-allyl-1,3-benzodioxole
PubChem Data safrole
WIPO International Patent Classification