4180-23-8 Usage
Description
(E)-Anethol is a phenylpropanoid that has been found in P. anisum seed oil and has antifungal and antioxidant activity. It is active against fermentatively growing S. cerevisiae under hypoxic, but not normoxic, conditions (MIC = 100 μg/ml), and against C. parapsilosis when used at a concentration of 15% w/w. (E)-Anethol has antioxidant activity in a Trolox equivalent antioxidant capacity (TEAC) assay but does not scavenge 2,2-diphenyl-1-picrylhydrazel (DPPH) radicals in a cell-free assay.
Chemical Properties
trans-anethole is a clear colorless to pale yellow liquid and has a characteristic anise, sweet, spicy, warm odor and corresponding sweet taste.
Anethole (1-methoxy-4-propenyl-benzene, isoestragole) is an alkoxypropenylbenzene derivative and an important favoring component of essential oils of more than 20 plant species. Essential oils from seeds of anise (Pimpinellaanisum L.), star anise (Illicium verum Hook.f), and sweet fennel (Foeniculum vulgare Mill. var. dulce) are the main sources used for the isolation of anethole. Two isomers of anethole occur in nature: E- or trans-anethole and Z-or cis-anethole. About 90 % of natural anethole is trans-isomer. Besides separation from natural essential oils, anethole is obtained using the rectification of crude sulfate turpentine and/or the organic synthesis starting from methylchavicol or anisole and propionic anhydride. Compared to natural compound, synthetic trans-anethole is impurified with higher amounts of cis-isomer.
Occurrence
Anethole is methyl ether of oestrone and has been found in fennel, aniseed, coriander, and many other volatile oils.
Uses
Different sources of media describe the Uses of 4180-23-8 differently. You can refer to the following data:
1. flavoring agent in food, dentifrices, etc.; in perfumery for soap, etc.; in pharmaceuticals as flavor; in photography and in
embedding materials in microscopy; some perfumery uses (fennei; absinthe; Hyacinth jacinthe; detergents; magnolia). Natural
occurrence: star anise
2. platelet aggregation inhibitor
3. trans-Anethole is used to inhibits lung and forestomach carcinogenesis, used as carbon and energy supplement in the culture media of Pseudomonas putida strain. It is also used as used as a flavoring substance.
Preparation
Different sources of media describe the Preparation of 4180-23-8 differently. You can refer to the following data:
1. 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%.
2. By isomerization of estragole using alcoholic potassium hydroxide as agent (Arctander, 1969).
Taste threshold values
Taste characteristics at 10 ppm: sweet, anise, licorice and spicy with a lingering, sweet aftertaste.
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
General Description
trans-Anethole is a naturally occuring flavouring agent. It has insecticidal, larvicidal, and antimicrobial properties.
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
METHODS OF BORYLATION AND USES THEREOF
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Page/Page column 61-62, (2021/04/30)
The present invention relates, in general terms, to methods of borylation and uses thereof. In particular, the present invention provides a method of borylating an alkene compound by contacting the compound with a boron compound, a Fe pre-catalyst and a protic additive. The borylation occurs at a vicinal (β) position to an electron donating or electron withdrawing moiety of the compound.
Highly Z-Selective Double Bond Transposition in Simple Alkenes and Allylarenes through a Spin-Accelerated Allyl Mechanism
Kim, Daniel,Pillon, Guy,Diprimio, Daniel J.,Holland, Patrick L.
supporting information, p. 3070 - 3074 (2021/03/08)
Double-bond transposition in alkenes (isomerization) offers opportunities for the synthesis of bioactive molecules, but requires high selectivity to avoid mixtures of products. Generation of Z-alkenes, which are present in many natural products and pharmaceuticals, is particularly challenging because it is usually less thermodynamically favorable than generation of the E isomers. We report a β-dialdiminate-supported, high-spin cobalt(I) complex that can convert terminal alkenes, including previously recalcitrant allylbenzenes, to Z-2-alkenes with unprecedentedly high regioselectivity and stereoselectivity. Deuterium labeling studies indicate that the catalyst operates through a π-allyl mechanism, which is different from the alkyl mechanism that is followed by other Z-selective catalysts. Computations indicate that the triplet cobalt(I) alkene complex undergoes a spin state change from the resting-state triplet to a singlet in the lowest-energy C-H activation transition state, which leads to the Z product. This suggests that this change in spin state enables the catalyst to differentiate the stereodefining barriers in this system, and more generally that spin-state changes may offer a route toward novel stereocontrol methods for first-row transition metals.
Facile Synthesis of Chiral Arylamines, Alkylamines and Amides by Enantioselective NiH-Catalyzed Hydroamination
Meng, Lingpu,Yang, Jingjie,Duan, Mei,Wang, You,Zhu, Shaolin
supporting information, p. 23584 - 23589 (2021/09/28)
Regio- and enantioselective hydroarylamination, hydroalkylamination and hydroamidation of styrenes have been developed by NiH catalysis with a simple bioxazoline ligand under mild conditions. A wide range of enantioenriched benzylic arylamines, alkylamines and amides can be easily accessed by nitroarenes, hydroxylamines and dioxazolones, respectively as amination reagents. The chiral induction in these reactions is proposed to proceed through an enantiodifferentiating syn-hydronickellation step.