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1-(4-Methoxyphenyl)-4,4-dimethyl-1-penten-3-one, also known as Heliotropin, is an organic compound with the molecular formula C14H18O2. It is a colorless to pale yellow liquid with a floral, sweet, and tenacious odor. This chemical is widely used in the fragrance industry as a fixative and in the synthesis of various perfumes, soaps, and cosmetics. Heliotropin is also employed as a flavoring agent in food and beverages, imparting a vanilla-like taste. It is derived from the reaction of p-anisaldehyde with acetone in the presence of an acid catalyst, followed by dehydration. Due to its complex structure and unique properties, 1-(4-Methoxyphenyl)-4,4-dimethyl-1-penten-3-one plays a significant role in the chemical and pharmaceutical industries.

2419-67-2

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2419-67-2 Usage

Check Digit Verification of cas no

The CAS Registry Mumber 2419-67-2 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 2,4,1 and 9 respectively; the second part has 2 digits, 6 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 2419-67:
(6*2)+(5*4)+(4*1)+(3*9)+(2*6)+(1*7)=82
82 % 10 = 2
So 2419-67-2 is a valid CAS Registry Number.
InChI:InChI=1/C14H18O2/c1-14(2,3)13(15)10-7-11-5-8-12(16-4)9-6-11/h5-10H,1-4H3/b10-7+

2419-67-2SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 18, 2017

Revision Date: Aug 18, 2017

1.Identification

1.1 GHS Product identifier

Product name (E)-1-(4-methoxyphenyl)-4,4-dimethylpent-1-en-3-one

1.2 Other means of identification

Product number -
Other names 1-<4-Methoxy-phenyl>-4,4-dimethyl-pent-1-en-3-on

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:2419-67-2 SDS

2419-67-2Relevant articles and documents

Alkene Synthesis by Photo-Wolff-Kischner Reaction of Sulfur Ylides and N-Tosylhydrazones

Gao, Pan-Pan,Yan, Dong-Mei,Bi, Ming-Hang,Jiang, Min,Xiao, Wen-Jing,Chen, Jia-Rong

, p. 14195 - 14201 (2021/09/20)

A visible-light-driven and room temperature photo-Wolff-Kischner reaction of sulfur ylides and N-tosylhydrazones has been developed for the first time to provide modular access to alkene synthesis. The high functional group tolerance and broad substrate scope were demonstrated by more than 60 examples. Both E- and Z-olefinic stereochemistry in the products could be controlled with excellent stereoselectivity. A series of mechanistic studies support that the reaction should proceed through a radical-carbanion crossover pathway, specifically involving addition of photo-generated sulfur ylide radical cations to N-tosylhydrazones to form carbanions and subsequent Wolff-Kischner process.

From Celecoxib to a Novel Class of Phosphodiesterase 5 Inhibitors: Trisubstituted Pyrazolines as Novel Phosphodiesterase 5 Inhibitors with Extremely High Potency and Phosphodiesterase Isozyme Selectivity

Abdel-Halim, Mohammad,Sigler, Sara,Racheed, Nora A. S.,Hefnawy, Amr,Fathalla, Reem K.,Hammam, Mennatallah A.,Maher, Ahmed,Maxuitenko, Yulia,Keeton, Adam B.,Hartmann, Rolf W.,Engel, Matthias,Piazza, Gary A.,Abadi, Ashraf H.

supporting information, p. 4462 - 4477 (2021/05/04)

A ligand-based approach involving systematic modifications of a trisubstituted pyrazoline scaffold derived from the COX2 inhibitor, celecoxib, was used to develop novel PDE5 inhibitors. Novel pyrazolines were identified with potent PDE5 inhibitory activit

Decarboxylation-triggered homo-Nazarov cyclization of cyclic enol carbonates catalyzed by rhenium complex

Kimaru, Natsuki,Komatsuki, Keiichi,Saito, Kodai,Yamada, Tohru

supporting information, p. 6133 - 6136 (2021/06/30)

Decarboxylative homo-Nazarov cyclization catalyzed by a Lewis acid was achieved using a cyclic enol carbonate bearing a cyclopropane moiety as a substrate. Various substrates were converted into the corresponding multi-substituted cyclohexenones in good yieldsviadecarboxylation, followed by 6-membered ring formation involving cyclopropane-ring-opening.

Discovery of trisubstituted pyrazolines as a novel scaffold for the development of selective phosphodiesterase 5 inhibitors

Abdel-Halim, Mohammad,Tinsley, Heather,Keeton, Adam B.,Weam, Mohammed,Atta, Noha H.,Hammam, Mennatallah A.,Hefnawy, Amr,Hartmann, Rolf W.,Engel, Matthias,Piazza, Gary A.,Abadi, Ashraf H.

, (2020/10/12)

Celecoxib, is a selective cyclooxygenase-2 (COX2) inhibitor with a 1,5-diaryl pyrazole scaffold. Celecoxib has a better safety profile compared to other COX2 inhibitors having side effects of systemic hypertension and thromboembolic complications. This may be partly attributed to an off-target activity involving phosphodiesterase 5 (PDE5) inhibition and the potentiation of NO/cGMP signalling allowing coronary vasodilation and aortic relaxation. Inspired by the structure of celecoxib, we synthesized a chemically diverse series of compounds containing a 1,3,5-trisubstituted pyrazoline scaffold to improve PDE5 inhibitory potency, while eliminating COX2 inhibitory activity. SAR studies for PDE5 inhibition revealed an essential role for a carboxylic acid functionality at the 1-phenyl and the importance of the non-planar pyrazoline core over the planar pyrazole with the 5-phenyl moiety tolerating a range of substituents. These modifications led to new PDE5 inhibitors with approximately 20-fold improved potency to inhibit PDE5 and no COX-2 inhibitory activity compared with celecoxib. PDE isozyme profiling of compound 11 revealed a favorable selectivity profile. These results suggest that trisubstituted pyrazolines provide a promising scaffold for further chemical optimization to identify novel PDE5 inhibitors with potential for less side effects compared with available PDE5 inhibitors used for the treatment of penile erectile dysfunction and pulmonary hypertension.

ALLOSTERIC INHIBITORS OF ATYPICAL PROTEIN KINASES C

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Paragraph 0086; 0108; 0120, (2015/06/08)

The invention provides specific small molecule compounds that allosterically regulate the activity of atypical protein kinase C, their use as a medicament, and their use in the treatment and prevention of allergic, inflammatory and autoimmune disorders, cancer, hyperproliferation, sepsis, viral and protozoan infections, dementing diseases, metabolic, sclerotic and osteoporotic disorders.

Discovery and optimization of 1,3,5-trisubstituted pyrazolines as potent and highly selective allosteric inhibitors of protein kinase C-χ

Abdel-Halim, Mohammad,Diesel, Britta,Kiemer, Alexandra K.,Abadi, Ashraf H.,Hartmann, Rolf W.,Engel, Matthias

supporting information, p. 6513 - 6530 (2014/10/15)

There is increasing evidence that the atypical protein kinase C, PKCχ, might be a therapeutic target in pulmonary and hepatic inflammatory diseases. However, targeting the highly conserved ATP-binding pocket in the catalytic domain held little promise to

One-pot synthesis of multifunctionalized cyclopropanes

Chang, Meng-Yang,Chen, Yi-Chia,Chan, Chieh-Kai

, p. 2257 - 2263 (2014/03/21)

A facile one-step synthetic protocol toward multifunctionalized cyclopropanes 4 is developed from substituted chalcones 1 and sulfones 2 in good yields via a [2C+1C] annulation.

NBS-mediated cyclization of trans-cinnamic alcohols

Chang, Meng-Yang,Tsai, Chung-Yu,Wu, Ming-Hao

, p. 6364 - 6370 (2013/07/26)

An efficient and straightforward three-step synthetic route toward 2,4-disubstituted-3-bromooxetanes 5 with the trans-trans contiguous stereogenic centers is developed from functionalized chalcones 3 via NaBH 4-mediated reduction of chalcones 3

Controlling the molecular topology of vinylogous iminium ions by logical substrate design: Highly regio- and stereoselective aminocatalytic 1,6-addition to linear 2,4-dienals

Silvi, Mattia,Chatterjee, Indranil,Liu, Yiankai,Melchiorre, Paolo

supporting information, p. 10780 - 10783 (2013/10/22)

All about topology control: The title reaction yields valuable tetrahydrofuran spirooxindoles (see scheme; TMS=trimethylsilyl), and exemplifies a rare asymmetric 1,6-addition to linear 2,4-dienals proceeding with high δ-site- and stereoselectivity. A steering group at the β-dienal position ensured molecular preorganization of the catalytically active vinylogous iminium ion intermediate for highly predictable reaction outcomes. Copyright

One-pot synthesis of multifunctionalized m-terphenyls

Chang, Meng-Yang,Chan, Chieh-Kai,Lin, Shin-Ying,Wu, Ming-Hao

, p. 9616 - 9624 (2013/10/22)

A facile one-step synthetic protocol toward multifunctionalized m-terphenyls 5 and sulfonyl m-terphenyls 6 is developed from substituted chalcones 1 and allyl sulfone 2 in good yields via a [3C+3C] annulation. The NaH-mediated annulation features transition metal catalyst-free condition. Chalcones 1 with the functional groups tolerance are easily prepared via Claisen-Schmidt condensation of substituted benzaldehydes 3 with acetophenone 4 in a qualitative yield under an aqueous alkaline methanolic solution.

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