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Xanthorrhizol is a natural sesquiterpenoid compound derived from the rhizome of Curcuma xanthorrhiza, a plant native to Southeast Asia. It is known for its potent bioactive properties, including its ability to induce apoptosis and growth arrest in certain cancer cells.

30199-26-9

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30199-26-9 Usage

Uses

Used in Anticancer Applications:
Xanthorrhizol is used as an anticancer agent, particularly effective against HCT116 human colon cancer cells. It demonstrates the ability to induce apoptosis (cell death) and growth arrest in these cells, making it a promising candidate for further research and potential therapeutic applications in the fight against colon cancer.
Used in Pharmaceutical Industry:
Xanthorrhizol is used as a bioactive compound in the pharmaceutical industry for its potential therapeutic effects. Its ability to target and affect cancer cells, as well as its natural origin, make it an attractive candidate for the development of new drugs and treatments for various diseases, including cancer.

Check Digit Verification of cas no

The CAS Registry Mumber 30199-26-9 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 3,0,1,9 and 9 respectively; the second part has 2 digits, 2 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 30199-26:
(7*3)+(6*0)+(5*1)+(4*9)+(3*9)+(2*2)+(1*6)=99
99 % 10 = 9
So 30199-26-9 is a valid CAS Registry Number.
InChI:InChI=1/C15H22O/c1-11(2)6-5-7-12(3)14-9-8-13(4)15(16)10-14/h6,8-10,12,16H,5,7H2,1-4H3/t12-/m1/s1

30199-26-9SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name 2-methyl-5-[(2R)-6-methylhept-5-en-2-yl]phenol

1.2 Other means of identification

Product number -
Other names EINECS 250-090-2

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:30199-26-9 SDS

30199-26-9Relevant academic research and scientific papers

Preparation of [kisantorizoru[kisantorizoru]

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Paragraph 0076-0078, (2020/09/12)

[Problem] an easy operation, can be obtained in a high yield of high-purity [kisantorizoru[kisantorizoru][kisantorizoru[kisantorizoru] preparation. [Solution] a method for preparing [kisantorizoru[kisantorizoru], amino acids in the presence of a condensation agent in a solvent extract curcuma [kisantoriza[kisantoriza] · stirring, the reaction mixture obtained in the step [kisantorizoruamino[kisantorizoruamino] acid ester, the reaction mixture, a mixture solution was prepared by adding ester-based solvent, the mixture was extracted with water under acidic conditions process, and the water contained in the hydrolyzed ester is extracted [kisantorizoruamino[kisantorizoruamino] extract, [kisantorizoru[kisantorizoru] comprises obtaining, [kisantorizoru[kisantorizoru] preparation. [Drawing] no

Cobalt-Catalyzed Enantioselective Negishi Cross-Coupling of Racemic α-Bromo Esters with Arylzincs

Liu, Feipeng,Zhong, Jiangchun,Zhou, Yun,Gao, Zidong,Walsh, Patrick J.,Wang, Xueyang,Ma, Sijie,Hou, Shicong,Liu, Shangzhong,Wang, Minan,Wang, Min,Bian, Qinghua

supporting information, p. 2059 - 2064 (2018/02/14)

The first cobalt-catalyzed enantioselective Negishi cross-coupling reaction, and the first arylation of α-halo esters with arylzinc halides, are disclosed. Employing a cobalt-bisoxazoline catalyst, various α-arylalkanoic esters were synthesized in excellent enantioselectivities and yields (up to 97 % ee and 98 % yield). A diverse range of functional groups, including ether, halide, thioether, silyl, amine, ester, acetal, amide, olefin and heteroaromatics is tolerated by this method. This method was suitable for gram-scale reactions, enabling the synthesis of (R)-xanthorrhizol with high enantiopurity. Radical clock experiments support the intermediacy of radicals.

Preparation and use of enantioenriched 2-aryl-propylsulfonylbenzene derivatives as valuable building blocks for the enantioselective synthesis of bisabolane sesquiterpenes

Serra, Stefano

, p. 1561 - 1572 (2015/02/05)

We have demonstrated that different enantioenriched 2-arylpropylsufonylbenzene derivatives are very useful building blocks for the synthesis of aromatic bisabolane sesquiterpenes. Their preparation and the exploitation of their chemical reactivity have been comprehensively investigated. Accordingly, the naturally occurring bisabolane sesquiterpenes (-)-curcuphenol, (-)-xanthorrhizol, (+)-glandulone A, (+)-curcudiol, (+)-turmerone and (+)-curcudiol-10-one were synthesized in high enantiomeric purity. It is worth noting that the compounds (+)-curcudiol-10-one and (+)-glandulone A were prepared in enantioenriched form for the first time. Through the proposed synthetic approaches, we were able to confirm both chemical structures and the absolute configurations previously assigned to the two aforementioned sesquiterpenes.

Enantioselective iridium-catalyzed hydrogenation of β,γ- unsaturated carboxylic acids: An efficient approach to chiral 4-alkyl-4-aryl butanoic acids

Song, Song,Zhu, Shou-Fei,Yang, Shuang,Li, Shen,Zhou, Qi-Lin

supporting information; experimental part, p. 2708 - 2711 (2012/04/17)

Chiral acids: A highly enantioselective iridium-catalyzed hydrogenation of β,γ-unsaturated carboxylic acids is developed for the preparation of chiral 4-alkyl-4-aryl butanoic acids (see scheme). Copyright

The first enantiospecific synthesis of (-)-heritol: absolute configuration determination

Chavan, Subhash P.,Thakkar, Mahesh,Kalkote, Uttam R.

, p. 643 - 646 (2007/10/03)

The first enantiospecific synthesis of (-)-heritol, from naturally occurring (R)-(+)-citronellal and confirmation of its absolute configuration, is described.

An enantiospecific synthesis of (+)-isoparvifolinone and (-)-parvifoline

Chavan, Subhash P.,Thakkar, Mahesh,Kalkote, Uttam R.

, p. 535 - 537 (2007/10/03)

An enantiospecific synthesis of (+)-isoparvifolinone and (-)-parvifoline, from naturally occurring (R)-(+)-citronellal, employing intramolecular Friedel-Crafts acylation as the key step, is described.

Synthesis of (R)-curcumene and (R)-xanthorrizol based on 1,2-aryl migration via phenonium ion

Ehara, Takeru,Tanikawa, Shin,Ono, Machiko,Akita, Hiroyuki

, p. 1361 - 1364 (2008/03/11)

Solvolysis reaction of methyl (4S,5S)-4-(4′-methoxyphenyl)-5- tosyloxy-2(E)-hexenoate 5 in water-saturated MeNO2 gave the 1,2-migration product, (4S,5S)-5-hydroxy-4-(4′-methoxyphenyl)-2-(E)- hexenoate 6 (55% yield), which was converted to methyl (R)-(4′- methylphenyl)hexanoate 11 in 25% overall yield (5 steps). Treatment of (R)-11 with MeLi gave tertiary alcohol congener 12, which was subjected to dehydration to afford (R)-(-)-curcumene 1. An introduction of hydroxyl group at meta-position of the aromatic ring in (R)-11 was achieved based on consecutive treatment [1) selective iodination, 2) conversion of aryl iodide to aryl boronate, 3) conversion of aryl boronate to phenol]. Thus obtained phenol (R)-16 was treated with MeLi to give tertiary alcohol congener 17, which was subjected to dehydration to afford (R)-(-)-xanthorrizol 2.

An enantiocontrolled total synthesis of (-)-xanthorrhizol

Sato, Kenji,Bando, Toshikazu,Shindo, Mitsuru,Shishido, Kozo

, p. 11 - 15 (2007/10/03)

An efficient and enantiocontrolled total synthesis of natural (-)- xanthorrhizol (3) has been accomplished by employing the lipase-mediated asymmetric acetylation of the σ-symmetrical prochiral 2-aryl-1,3-propanediol (7) leading to the formation of the optically enriched monoacetate (6) as the key step.

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