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Anethole

HCID 637563
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Basic information

CAS
104-46-1
Standard SMILES
C/C=C/c1ccc(OC)cc1
InChIKey
RUVINXPYWBROJD-ONEGZZNKSA-N
Molecular formula
C10H12O
Average molar mass
148.2 g/mol
Monoisotopic mass
148.088815

Overview

Anethole appears as white crystals or a liquid. Odor of anise oil and a sweet taste. (NTP, 1992)

Names & identifiers

Preferred name
Anethole
IUPAC
1-methoxy-4-[(E)-prop-1-enyl]benzene
English name
cis-Anethol
Molecular formula
C10H12O
Molecular weight
148.2

Names & synonyms

ANETHOLE104-46-1Anise camphorMonasirupAnethol4-PropenylanisoleAnisole, p-propenyl-trans-p-Propenylanisolep-Anethole1-Methoxy-4-(1-propenyl)benzeneAniskampfertrans-1-p-Anisylpropene
Show more names
SYNTHETIC ANETHOLEFEMA 2086IsoestragoleNatural AnetholePARA METHOXY ALPHA PHENYL PROPENEAnethole NatANETHOLE 21/22
Anethole, trans1-methoxy-4-[(E)-prop-1-enyl]benzenep-1-Propenylanisole1-Methoxy-4-propenylbenzene4-MethoxypropenylbenzeneBenzene, 1-methoxy-4-(1-propenyl)-p-Propenylphenyl methyl etherFEMA No. 2086

Database identifiers

CAS
104-46-1、4180-23-8、50770-19-9
PubChem CID
637563
DTXSID
DTXSID9020087
ChEMBL
CHEMBL452630
ChEBI
CHEBI:2716
UNII
Q3JEK5DO4K
EC Number
203-205-5、224-052-0、256-753-2
Nikkaji
J4.026F、J61.645A

Properties

Computed structural properties

XLogP
3.3
Topological polar surface area
9.2 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
1
Rotatable bonds
2
Heavy atoms
11
Formal charge
0
Complexity
121

Experimental & physicochemical properties

Chemical ClassesOther Classes -> Other Aromatic Compounds
DrugsPharmaceuticals
Cosmetics · 2 items

Cosmetics ingredient -> Flavor; Fragrance; Other (Specify)

Denaturant

SpringerMaterials PropertiesBoiling point
Fragrances · 2 items

Fragrance Ingredient (Anethole (isomer unspecified)) -> IFRA transparency List

Fragrance Ingredient (trans-Anethole) -> IFRA transparency List

Pesticides · 2 items

Agrochemicals -> Pesticide active substances

Active substance -> EU Pesticides database: Not approved

OdorANISE OIL ODOR
TasteSWEET TASTE
Food AdditivesFLAVORING AGENT OR ADJUVANT -> FDA Substance added to food
Density

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

GHS classification

GHS Classification · 6 items

This chemical does not meet GHS hazard criteria for 2.9% (55 of 1880) of reports.

Warning

H317 (95.3%): May cause an allergic skin reaction [Warning Sensitization, Skin]

P261, P272, P280, P302+P352, P321, P333+P317, P362+P364, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 1880 reports by companies from 19 notifications to the ECHA C&L Inventory.

This chemical does not meet GHS hazard criteria for 6.2% (20 of 321) of reports.

Hazard information

Regulatory Information · 6 items

Chemical: Benzene, 1-methoxy-4-(1-propenyl)-

Chemical: Benzene, 1-methoxy-4-(1-propenyl)-, (E)-

Hazard Traits - Fragrance Allergen

Regulation (EC) No 1831/2003 (amended)

Benzene, 1-methoxy-4-(1-propen-1-yl)- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Benzene, 1-methoxy-4-(1-propen-1-yl)- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

Benzene, 1-methoxy-4-(1E)-1-propen-1-yl- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Benzene, 1-methoxy-4-(1E)-1-propen-1-yl- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

Other Safety InformationIMAP assessments - Benzene, 1-methoxy-4-(1-propenyl)-, (E)-: Human health tier II assessment
DOT LabelCombustible Liquid
Fire HazardsThis compound is combustible. (NTP, 1992)
Health Hazards

Chemistry & industry

Pharmacology

Metabolism/Metabolites · 3 items

ANETHOLE YIELDS PARA-PROPENYLPHENOL IN RABBIT, MOUSE, GUINEA PIG, & DOG. ANETHOLE YIELDS PARA-PROPENYLPHENOL IN RAT. /FROM TABLE/

ANETHOLE YIELDS ANISIC ACID IN MAN, RABBIT, & RAT. ANETHOLE YIELDS PARA-METHOXYCINNAMYL ALCOHOL IN RAT.

OXIDATIVE O-DEMETHYLATION LEADING TO P-HYDROXYPROPENYLBENZENE & P-HYDROXYCINNAMIC ACID WAS FOUND TO BE A MAJOR BIOTRANSFORMATION OF ANETHOLE. METABOLISM VIA CINNAMOYL DERIV WAS MORE EXTENSIVE WITH THE PROPENYL SUBSTITUENT THAN FOR THE ALLYL COMPD; & FURTHER METABOLISM BY BETA-OXIDATION ALSO OCCURRED.

MeSH Pharmacological ClassificationSubstances added to foods and medicine to improve the taste.
Absorption, Distribution and Excretion · 5 items

/IN BIOTRANSFORMATION OF ANETHOLE/...ANISIC ACID...CONSTITUTED THE MAJOR URINARY METABOLITE. ...THERE WAS A QUANTITATIVE RECOVERY OF THE DOSE ADMIN.

TRANS-ANETHOLE WAS AMONG 4 FOOD ADDITIVES STUDIED & FOUND LARGELY ABSORBED FROM DIGESTIVE TRACT BY PASSIVE DIFFUSION. ABSORPTION KINETICS VARY PARTIALLY BY DIFFERENCES OF COMPD IN COEFFICIENTS OF LIPOSOLUBILITY.

...TRANS-ANETHOLE USED IN PREPN OF ANIS-FLAVORED ALCOHOLIC BEVERAGES WAS STUDIED IN THE RABBIT & RAT AFTER IV & ORAL ADMIN. IT WAS EXCRETED RAPIDLY FROM THE ANIMAL REGARDLESS OF /ROUTE/ OF ADMIN. AFTER IV INJECTION, IT WAS FOUND CONCENTRATED IN LIVER, LUNGS & BRAIN; AFTER ORAL ADMIN...MOST OF IT REMAINED IN STOMACH.

TRANS-ANETHOLE IS ONE OF THE COMPOUNDS LARGELY ABSORBED FROM THE DIGESTIVE TRACT BY MECHANISM OF PASSIVE DIFFUSION.

THE METABOLITES OF ANETHOLE IN RATS WERE IDENTIFIED AND DETERMINED. MOST OF THE URINARY METABOLITES WERE ALSO DETECTED IN THE BILE.

Uses & manufacturing

Uses · 6 items

Chief constituent of anise, star anise, and fennel oils; Used as a flavoring agent (foods, beverages, and drugs) and fragrance (soaps and dentifrices); [Merck Index] Used to make anisaldehyde, as a sensitizer in bleaching colors in photography, an embedding material in microscopy, and an insect attractant; [HSDB]

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Compound notes

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· 3 items

0.9882 (NTP, 1992) - Less dense than water; will float

0.9878 @ 20 °C/4 °C

0.983-0.988

Flavoring AgentsEU Flavoring substances
Viscosity2.45X10-3 Pa.s

Physicochemical properties

Melting point
20 to · 20 to 21 °C (68 to 70 °F; 293 to 294 K)
Boiling point
234 °C · 234 °C (453 °F; 507 K) ; 81 °C (178 °F; 354 K) at 2 mmHg
Density
0.998 g/cm3 · 0.998 g/cm3
refractive index
20 · n20/D 1.561(lit.)
FLAVIS Number
4.088 · 04.088 | 1-Methoxy-4-(1-propenyl)benzene
Flash point
195 °F · 195 °F
storage temp.
2 · Sealed in dry,2-8°C
solubility
30 mg/ml; · DMSO: 30 mg/ml; PBS (pH 7.2): 10 mg/ml
form
Oil
color
Colorless to off-white
Odor
100 % · at 100.00 %. sweet anise licorice medicinal
Odor Type
licorice
Water Solubility
148.2 mg/L · 148.2mg/L(25 ºC)
Henry's Law Constant
9.9 · 9.9×10-2 mol/(m3Pa) at 25℃, Roon et al. (2005)
Stability
Stable. Combustible. Incompatible with strong oxidizing agents.
Cosmetics Ingredients Functions
FRAGRANCEDENATURANT
LogP
3.39 · 3.39
CAS DataBase Reference
104 · 104-46-1(CAS DataBase Reference)
FDA UNII
79 C64YD3Q · A79C64YD3Q
NIST Chemistry Reference
1 · Benzene, 1-methoxy-4-(1-propenyl)-(104-46-1)
EPA Substance Registry System
Anethole (104-46-1)
Symbol(GHS)
7 · GHS07
Signal word
Warning
Hazard statements
317 · H317
Precautionary statements
261 · P261-P280
Hazard Codes
Xi,Xn
Risk Statements
43 · 43-36/37/38-20/21/22
Safety Statements
36 · 36/37-36-26
WGK Germany
2 · 2
RTECS
9275000 · BZ9275000
F
8 · 8
TSCA
TSCA listed
Hazardous Substances Data
104 · 104-46-1(Hazardous Substances Data)
ACUTE/CHRONIC HAZARDS: Toxic. (NTP, 1992)
Hazards Summary · 1 item

A mutagen and tumorigen; Causes hepatitis, somnolence, and coma in high-dose feeding studies of rats; [RTECS] Fennel oil is toxic by ingestion--may cause vomiting, seizures, and pulmonary edema; [HSDB] Food handlers may develop contact dermatitis to anethole; [Kanerva, p. 1752] May cause irritation; [MSDSonline]

FDA Requirements · 2 items

Anethole used as a synthetic flavoring substance or adjuvant in food for human consumption is generally recognized as safe when used in accordance with good manufacturing practice.

Anethole used as a synthetic flavoring substance or adjuvant in animal drugs, feeds, and related products is generally recognized as safe when used in accordance with good manufacturing or feeding practice.

Reactive GroupEthers
FIFRA Requirements · 1 item

As the federal pesticide law FIFRA directs, EPA is conducting a comprehensive review of older pesticides to consider their health and environmental effects and make decisions about their future use. Under this pesticide reregistration program, EPA examines health and safety data for pesticide active ingredients initially registered before November 1, 1984, and determines whether they are eligible for reregistration. In addition, all pesticides must meet the new safety standard of the Food Quality Protection Act of 1996. Pesticides for which EPA had not issued Registration Standards prior to the effective date of FIFRA, as amended in 1988, were divided into three lists based upon their potential for human exposure and other factors, with List B containing pesticides of greater concern and List D pesticides of less concern. p-Anethole is found on List C. Case No: 3018; Pesticide type: Rodenticide; Case Status: No products containing the pesticide are actively registered ... The case /is characterized/ as "cancelled." Under FIFRA, pesticide producers may voluntarily cancel their registered products. EPA also may cancel pesticide registrations if registrants fail to pay required fees or make/meet certain reregistration commitments, or if EPA reaches findings of unreasonable adverse effects.; Active ingredient (AI): Anethole; AI Status: The active ingredient is no longer contained in any registered pesticide products ... "cancelled."

Reactivity ProfileProtect from light (NTP, 1992).
Air and Water ReactionsSlightly water soluble (NTP, 1992).
Hazard Classes and Categories · 3 items

Skin Sens. 1B (95.3%)

Skin Sens. 1 (93.8%)

Skin sensitisation - category 1

Safety & protection

Fire FightingTo extinguish a fire involving this chemical you may use a dry chemical, carbon dioxide, foam or halon extinguisher; a water spray may also be used. (NTP, 1992)
First Aid · 1 item

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.

Nonfire Spill Response · 1 item

SMALL SPILLS AND LEAKAGE: Use absorbent paper to pick up spill material. Contaminated clothing and absorbent paper should be sealed in a vapor-tight plastic bag for eventual disposal. Solvent-wash contaminated surfaces with alcohol followed by washing with a strong soap and water solution.

Disposal Methods · 1 item

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

Isolation and EvacuationExcerpt from ERG Guide 128 [Flammable Liquids (Water-Immiscible)]:
Personal Protective Equipment (PPE)MINIMUM PROTECTIVE CLOTHING: When working with this chemical, you should wear impervious coveralls, shoe covers and gloves.

Toxicology

Body BurdenAnethole was discovered in one out of 46 samples of human adipose tissue (age class: 0-14 yrs and North Central region(1).
InteractionsMEAN SLEEPING TIME IN MICE TREATED WITH 50 MG/KG NA-PENTOBARBITAL ABOUT DOUBLED WITH 20 & 50 MG OF SOME COMPD; ANETHOLE WAS LESS ACTIVE.
Environmental Fate · 3 items

TERRESTRIAL FATE: Anethole will have a medium to low mobility(3) in soil based on estimated Koc values ranging from 327 to 680(1,2). Insufficient data are available to predict the relative importance or rate of biodegradation in soil conditions(SRC).

AQUATIC FATE: Volatilization of anethole from water is not rapid but could possibly be significant based upon estimated Henry's Law constant of 7.18X10-5 atm cu m/mol(1,2,SRC). Volatilization half-lives from a model river (1 m deep flowing 1 m/sec with a wind velocity of 3 m/sec) and a model lake (1 meter deep) can be estimated to be about 18 hours and 9 days respectively(2). Insufficient data are available to predict the relative importance or rate of biodegradation from natural waters(SRC). Aquatic bioconcentration is not expected to be an important fate process, however, based on a Koc value of 680(3), some absorption to sediment may occur(SRC).

ATMOSPHERIC FATE: Based on an extrapolated vapor pressure of approximately 0.005 mm Hg at 25 °C(1), anethole will exist in the atmosphere in the vapor phase(2). It will degrade in the atmosphere by reaction with photochemically produced hydroxyl radicals with estimated half-lives of 4.9 and 4.5 hrs for the cis and trans isomers, respectively(3). Anethole will also degrade in the atmosphere by reaction with atmospheric ozone with estimated half-lives of 4.03 and 2.02 hrs for the cis and trans isomers, respectively(3).

Food Survey ValuesAn analysis of chickpea seed, found a 0.9% constituent of anethole(1).
Adverse EffectsNeurotoxin - Other CNS neurotoxin
Effluent Concentrations · 1 item

In a monitoring study of organic constituents of kraft mill aerated stabilization basins in Oregon, anethole was detected at trace quantities (detection limits were not reported)(1). Another study of kraft mill aerated lagoons also identified anethole in four samples of an unbleached kraft aerated lagoon influent and effluent in the following concentrations (ppb): 30-60, 20-10, 30-trace (detection limit not reported), and 20-10; influents and effluents respectively(2). A third study of unbleached treated kraft paper mill wastewater in Georgia found anethole at approximately 0.007 mg/l(3).

Soil Adsorption/Mobility · 1 item

Using a structure estimation method based on molecular connectivity indexes, the Koc for anethole can be estimated to be about 680(1). The Koc for anethole can be estimated to be about 327 based on an experimental water solubility of 111 mg/L(3) and a regression derived equation(2). According to a suggested classification scheme(4), these estimated Koc values suggest that anethole has medium to low soil mobility.

Natural Pollution SourcesAnethole occurs naturally in anise, star anise, and fennel oils(1) and chickpea seed(2).
Human Toxicity Excerpts · 4 items

A CASE OF STOMATITIS HAS BEEN REPORTED AFTER USE OF DENTURE CREAM CONTAINING OIL OF ANISE (80-90% ANETHOLE). APPLIED TO SKIN ANETHOLE CAUSES ERYTHEMA, SCALING & VESICULATION.

COMPARED WITH RESULTS OF TESTS WITH BALSAMS & OTHER ESSENTIAL OILS, STAR OF ANISE OIL DOES NOT GIVE CROSS-REACTION & PSEUDO CROSS-SENSITIVITY. PT POSITIVE TO THIS OIL ARE FREQUENTLY POSITIVE TO ANETHOLE.

ANETHOLE TESTED @ 2% IN PETROLATUM PRODUCED NO IRRITATION AFTER A 48-HR CLOSED PATCH TEST IN 25 HUMAN SUBJECTS. A MAXIMIZATION TEST WAS CARRIED OUT ON 25 VOLUNTEERS. MATERIAL WAS TESTED @ 2% CONCN IN PETROLATUM & PRODUCED NO REACTIONS.

ANETHOLE WAS THE MOST SENSITIZING OF APPROX 8 SENSITIZING COMPONENTS. SYNERGISM MAY HAVE BEEN INVOLVED IN THE IRRITATING & SENSITIZING PROPERTIES.

Artificial Pollution Sources · 1 item

Chloronitrobenzenes are produced by nitration of chlorobenzene. The crude chloronitrobenzene obtained from the nitration process contains about 34% o-chloronitrobenzene, 65% p-chloronitrobenzene, and 1% m-chloronitrobenzene. The isomers are separated by a combination of crystallization and distillation.

Drug Induced Liver Injury · 4 items

Drug-Induced Liver Injury Severity and Toxicity (DILIst)

Anethole

DILI Positive

DOI:10.1016/j.drudis.2019.09.022

Environmental Bioconcentration · 1 item

Based upon an experimental water solubility of 111 mg/l(1), the BCF of anethole can be estimated to be approximately 43.4 from a regression-derived equation(2). This estimated BCF value suggests that bioconcentration in aquatic organisms is not expected to be an important fate process(SRC).

Regulatory information

FDA Requirements · 2 items

Anethole used as a synthetic flavoring substance or adjuvant in food for human consumption is generally recognized as safe when used in accordance with good manufacturing practice.

Anethole used as a synthetic flavoring substance or adjuvant in animal drugs, feeds, and related products is generally recognized as safe when used in accordance with good manufacturing or feeding practice.

FIFRA Requirements · 1 item

As the federal pesticide law FIFRA directs, EPA is conducting a comprehensive review of older pesticides to consider their health and environmental effects and make decisions about their future use. Under this pesticide reregistration program, EPA examines health and safety data for pesticide active ingredients initially registered before November 1, 1984, and determines whether they are eligible for reregistration. In addition, all pesticides must meet the new safety standard of the Food Quality Protection Act of 1996. Pesticides for which EPA had not issued Registration Standards prior to the effective date of FIFRA, as amended in 1988, were divided into three lists based upon their potential for human exposure and other factors, with List B containing pesticides of greater concern and List D pesticides of less concern. p-Anethole is found on List C. Case No: 3018; Pesticide type: Rodenticide; Case Status: No products containing the pesticide are actively registered ... The case /is characterized/ as "cancelled." Under FIFRA, pesticide producers may voluntarily cancel their registered products. EPA also may cancel pesticide registrations if registrants fail to pay required fees or make/meet certain reregistration commitments, or if EPA reaches findings of unreasonable adverse effects.; Active ingredient (AI): Anethole; AI Status: The active ingredient is no longer contained in any registered pesticide products ... "cancelled."

Safety data

F
8
wgk
2
tsca
TSCA listed
rtecs
BZ9275000
risk_code
43-36/37/38-20/21/22
Signal word
Warning
Symbol(GHS)
GHS07
hazard_code
Xi,Xn
safety_code
36/37-36-26
Hazard statements
H317
Precautionary statements
P261-P280
Hazardous Substances Data
104-46-1(Hazardous Substances Data)

Photographic Processing [Category: Other]

The active ingredient is no longer contained in any registered pesticide products ... "cancelled."

MFR ANISALDEHYDE; IN PERFUMERY, SOAP & DENTIFRICES; SENSITIZER IN BLEACHING COLORS IN COLOR PHOTOGRAPHY; AS EMBEDDING MATERIAL IN MICROSCOPY; PHARMACEUTIC AID (FLAVOR); VET: HAS BEEN USED AS A CARMINATIVE & AS A FLAVORING AGENT

AS FLAVOR INGREDIENT

IN LICORICE CANDIES

U.S. Production · 3 items

2023: 2,063,610 lb

2023: 250,000 - <400,000 lb

(1991) 1,641,000 kg

Consumer UsesFragrance
Industry Uses · 2 items

Intermediate

Other

Methods of Manufacturing · 2 items

SYNTHESIS BY ESTERIFICATION OF P-CRESOL WITH METHYL ALCOHOL & SUBSEQUENT CONDENSATION WITH ACETALDEHYDE (PERKINS). ...MOST COMMON METHOD...FROM PINE OIL. BY FRACTIONAL DISTILLATION.../OF/ ESSENTIAL OILS OF ANISE, STAR ANISE & FENNEL. ...ANISE...CONTAIN...85% ANETHOLE; FENNEL FROM 60 TO 70%.

SEPN OF CIS & TRANS ISOMERS: NAVES ET AL, COMPT REND 246: 1734 (1958); BULL SOC CHIM FRANCE 1958, 566; HELY CHIM ACTA 43: 230 (1960); FERRONI ET AL, GAZZ CHIM ITAL 92: 1198 (1962). SYNTHESIS: MUELLER, ROSCHEISEN, BER 90: 543 (1957).

Formulations/PreparationsGRADES: USP (TECHNICAL); FCC (FOOD CHEMICALS CODEX).
Household Products · 3 items

Cosmetics product ingredient: 1-Methoxy-4-(1E)-1-propen-1-yl-benzene (trans-Anethole) (Anethole)

Information on 22 consumer products that contain Anethole in the following categories is provided:

Information on 45 consumer products that contain Trans-Anethole in the following categories is provided:

Use Classification · 6 items

Fragrance Ingredients

Fragrance Ingredients

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

Flavoring Agents -> JECFA Flavorings Index

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

General Manufacturing Information · 6 items

All Other Basic Organic Chemical Manufacturing

All Other Basic Organic Chemical Manufacturing

Benzene, 1-methoxy-4-(1-propen-1-yl)-: ACTIVE

Benzene, 1-methoxy-4-(1E)-1-propen-1-yl-: ACTIVE

Benzene, 1-methoxy-4-(propen-1-yl)-: INACTIVE

...THERE IS REGULAR USE OF COMPOUNDED ESSENTIAL OILS CONSISTING...OF...ANETHOL /IN MFR OF SWEET LIQUEURS/. ... THE EFFECTIVE YIELD OF ANETHOL, BASED ON THE FINISHED LIQUEUR "AS IS" IS APPROX 1:2000.

Applications · 4 items

DescriptionAnethole is the main component of anise, star anise and fennel oils. It is used in the food and cosmetic industries, in bleaching colors photography and as an embedding material. Is mainly a cause of intolerance to toothpaste but may cause contact dermatitis in food handlers.

HistoryIn China, anise has been used as a traditional food spice and seasoning. In the anise plant, the main biological active ingredient is volatile oils such as trans-anethole. Till the end of last century, several methods to obtain the pure anethole have been developed, including:1. Cooling, crystallizing, and recrystallizing after the distillation of the anise oil.2. Heating p-methoxyphenyl crotonic acid at 220–240°C.3. Heating and dehydrating the derived product of anisaldehyde and C2H5MgX.4. Heating anisaldehyde together with propionic anhydride and sodium propionate.5. Adding concentrated hydrochloric acid and phosphoric acid to the mixture of anisole and propionaldehyde at 0°C and then heating the product with pyridine to remove hydrogen chloride.6. Prepare Grignard reagent using parabromoanisole, then react with allyl bromide to produce p-methoxyphenylpropylene, then heat with potassium hydroxide, and finally anethole was obtained after isomerization.7. Using crystalline ferric chloride to catalyze the reaction of p-propenyl phenol and methanol .Anethole is easily oxidized when exposed in the air, especially in the presence of heat, light, or catalyst . Therefore, in recent years, a series of studies have been carried out on the synthesis of its derivatives in order to obtain more active substances.

UsesPromote the white blood cells proliferation

General DescriptionWhite crystals or a liquid. Odor of anise oil and a sweet taste.

Preparation methods · 1 item

PreparationProduction. Anethole is isolated from anethole-rich essential oils as well as from sulfate turpentine oils or is synthesized starting from anisole.1) Anethole can be obtained from oils in which it occurs as a major component (main source is star anise oil) by distillation and/or crystallization. 2) A fraction of American sulfate turpentine oil (0.5% of the total) consists mainly of an azeotropic mixture of anethole and caryophyllene. (E)-Anethole can be isolated from this mixture by crystallization. 3) Another fraction of American sulfate turpentine oil (1% of the total) consists essentially of an azeotropic mixture of estragole (l-methoxy-4-allylbenzene, bp101.3 kPa 216°C) and α-terpineol. Treatment with potassium hydroxide yields a mixture of anethole isomers and -terpineol, which can be separated by fractional distillation.4) Synthesis from anisole and propionic acid derivatives. Anisole is converted into 4-methoxypropiophenone by Friedel–Crafts acylation with propionyl chloride or propionic anhydride. The ketone is hydrogenated to the corresponding alcohol with a copper chromite catalyst.The alcohol is dehydrated in the presence of acidic catalysts to a (Z)-/(E)-mixture of anetholes.

Upstream & downstream products

Upstream raw materials

4-BromoanisoleAnise oilSodiumAnisoleFennel Oil1,4-Dimethoxybenzene4-Phenyl-1-butenep-AnisaldehydeAllyl bromidePropionic anhydrideSodium hydroxideEstragoleDimethyl etherAllylbenzeneCrotonic acidSodium propionate

Downstream products

Anethole trithionetrans-Anethole4-n-Propylanisolep-AnisaldehydeHEXESTROL4-Methoxy-beta-bromopropiophenone

Additional notes

DefinitionChEBI: A monomethoxybenzene that is methoxybenzene substituted by a prop-1-en-1-yl group at position 4.