4180-23-8 Usage
Description
Trans-Anethole, also known as (E)-Anethol, is a phenylpropanoid that is a naturally occurring flavoring agent. It is an alkoxypropenylbenzene derivative and an important favoring component of essential oils of more than 20 plant species. Trans-Anethole has insecticidal, larvicidal, and antimicrobial properties. It is a clear colorless to pale yellow liquid with a characteristic anise, sweet, spicy, warm odor and corresponding sweet taste.
Uses
Used in Flavoring Industry:
Trans-Anethole is used as a flavoring agent in the food and dentifrice industries due to its sweet, anise, licorice, and spicy taste with a lingering, sweet aftertaste.
Used in Perfumery:
Trans-Anethole is used in perfumery for soap and other products, as well as in some perfumes such as fennel, absinthe, and Hyacinth jacinthe.
Used in Pharmaceutical Industry:
Trans-Anethole is used as a flavor in the pharmaceutical industry and is also used in the culture media of Pseudomonas putida strain as a carbon and energy supplement.
Used in Photography and Microscopy:
Trans-Anethole is used in photography and as an embedding material in microscopy.
Used in Detergents:
Trans-Anethole is used in the production of detergents and has natural occurrence in star anise.
Used as a Platelet Aggregation Inhibitor:
Trans-Anethole is used to inhibit platelet aggregation, which can help prevent blood clots and related health issues.
Used in Anticancer Applications:
Trans-Anethole is used to inhibit lung and forestomach carcinogenesis, potentially offering therapeutic benefits in cancer treatment.
Used in Antifungal and Antioxidant Applications:
Trans-Anethole has been found to have antifungal and antioxidant activity, making it a useful compound in various applications.
Natural Occurrence:
Trans-Anethole is found in essential oils from seeds of anise (Pimpinella anisum L.), star anise (Illicium verum Hook.f), and sweet fennel (Foeniculum vulgare Mill. var. dulce). It is also found in fennel, aniseed, coriander, and many other volatile oils.
Preparation
By esterification of p-cresol with methyl alcohol and with subsequent condensation with α-cetaldehyde (Perknis); the
most common method of preparation is from pine oil. By fractional distillation of the essential oils of anise, star anise, and fennel;
the anise essences contain an average of 85% anethole; fennel, from 60 to 70%.
Preparation
By isomerization of estragole using alcoholic potassium hydroxide as agent (Arctander, 1969).
Synthesis Reference(s)
The Journal of Organic Chemistry, 50, p. 1797, 1985 DOI: 10.1021/jo00211a002Tetrahedron, 24, p. 2183, 1968 DOI: 10.1016/0040-4020(68)88120-7
Biochem/physiol Actions
Naturally occurring phenylpropene derivative that is estrogenic at lower concentrations and cytotoxic at higher concentrations to cancer cell lines. The cytotoxicity is related to the metabolism of trans-anethole to 4-hydroxy-1-propenylbenzene.
Anticancer Research
It is one of the major constituents of essential oil of fennel and anise and belongs tothe class of phenylpropenes. It has the capacity to block both inflammation andcarcinogenesis. It is an antioxidant and also a suppressor of NF-κB activation byIκBα degradation (Aggarwal and Shishodia 2004).
Metabolism
Anethole is metabolized by oxidation of the propenyl group and is excreted as anisic acid (Williams, 1959). The metabolism of trans-anethole used in the preparation of anis-flavoured alcoholic beverages was studied in the rabbit and rat after iv and oral administration. It was excreted rapidly from the animal regardless of the method of administration. After iv injection it was found concentrated in the liver, lungs and brain; after oral administration, absorption was slight and most of it remained in the stomach. Ethyl alcohol has no effect on the metabolism (Le Bourhis, 1968).
Check Digit Verification of cas no
The CAS Registry Mumber 4180-23-8 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 4,1,8 and 0 respectively; the second part has 2 digits, 2 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 4180-23:
(6*4)+(5*1)+(4*8)+(3*0)+(2*2)+(1*3)=68
68 % 10 = 8
So 4180-23-8 is a valid CAS Registry Number.
InChI:InChI=1/C10H12O/c1-3-4-9-5-7-10(11-2)8-6-9/h3-8H,1-2H3/b4-3+
4180-23-8Relevant articles and documents
Synthesis, Reactivity, and Coordination of Semihomologous dppf Congeners Bearing Primary Phosphine and Primary Phosphine Oxide Groups
Horky, Filip,Císa?ová, Ivana,?těpni?ka, Petr
, p. 427 - 441 (2021/02/06)
This contribution reports the synthesis of two phosphinoferrocene ligands desymmetrized by an inserted methylene spacer, viz., a bis-phosphine combining primary and tertiary phosphine moieties in its structure, Ph2PfcCH2PH2 (2), and a structurally unique, stable phosphine-primary phosphine oxide Ph2PfcCH2P(O)H2 (7; fc = ferrocene-1,1′-diyl). Compounds 2 and 7, together with 1,1′-bis(diphenylphosphino)ferrocene (dppf), the bis-tertiary phosphine Ph2PfcCH2PPh2, and the adduct Ph2P(BH3)fcCH2PH2 (6), were studied as ligands in Ru(II) complexes bearing auxiliary ν6-arene ligands and both free ligands and the isolated complexes were structurally authenticated, using spectroscopic methods and X-ray crystallography, and further investigated by cyclic voltammetry. The results suggest that distinct donor moieties in the unsymmetric ligands differentiate the otherwise identical coordinated metal centers and that the phosphine moiety in phosphine-phosphine oxide ligand 7 is preferably coordinated to Ru(II), before the phosphine oxide group, which must tautomerize into the hydroxyphosphine form prior to coordination.
A donor-acceptor complex enables the synthesis of: E -olefins from alcohols, amines and carboxylic acids
Chen, Kun-Quan,Shen, Jie,Wang, Zhi-Xiang,Chen, Xiang-Yu
, p. 6684 - 6690 (2021/05/31)
Olefins are prevalent substrates and functionalities. The synthesis of olefins from readily available starting materials such as alcohols, amines and carboxylic acids is of great significance to address the sustainability concerns in organic synthesis. Metallaphotoredox-catalyzed defunctionalizations were reported to achieve such transformations under mild conditions. However, all these valuable strategies require a transition metal catalyst, a ligand or an expensive photocatalyst, with the challenges of controlling the region- and stereoselectivities remaining. Herein, we present a fundamentally distinct strategy enabled by electron donor-acceptor (EDA) complexes, for the selective synthesis of olefins from these simple and easily available starting materials. The conversions took place via photoactivation of the EDA complexes of the activated substrates with alkali salts, followed by hydrogen atom elimination from in situ generated alkyl radicals. This method is operationally simple and straightforward and free of photocatalysts and transition-metals, and shows high regio- and stereoselectivities.
Electro-mediated PhotoRedox Catalysis for Selective C(sp3)–O Cleavages of Phosphinated Alcohols to Carbanions
Barham, Joshua P.,K?nig, Burkhard,Karl, Tobias A.,Reiter, Sebastian,Tian, Xianhai,Yakubov, Shahboz,de Vivie-Riedle, Regina
supporting information, p. 20817 - 20825 (2021/08/18)
We report a novel example of electro-mediated photoredox catalysis (e-PRC) in the reductive cleavage of C(sp3)?O bonds of phosphinated alcohols to alkyl carbanions. As well as deoxygenations, olefinations are reported which are E-selective and can be made Z-selective in a tandem reduction/photosensitization process where both steps are photoelectrochemically promoted. Spectroscopy, computation, and catalyst structural variations reveal that our new naphthalene monoimide-type catalyst allows for an intimate dispersive precomplexation of its radical anion form with the phosphinate substrate, facilitating a reactivity-determining C(sp3)?O cleavage. Surprisingly and in contrast to previously reported photoexcited radical anion chemistries, our conditions tolerate aryl chlorides/bromides and do not give rise to Birch-type reductions.