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5396-89-4

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5396-89-4 Usage

Description

Benzyl acetoacetate, also known as AAbenzyl, is a chemical intermediate derived from organic chemicals and is known for its sweet, floral, fresh, balsamic, and fruity odor, which is similar to that of ethyl acetate. It undergoes asymmetric bioreduction to form benzyl (S)-(+)-3-hydroxybutyrate in the presence of Candida schatavii strain MY 1831. Benzyl acetoacetate has been reported to be found in litchi (Litchi sinensis Sonn.).

Uses

Used in Pharmaceutical and Fine Chemical Industries:
Benzyl acetoacetate is used as a pharmaceutical and fine chemical intermediate for the synthesis of various organic chemicals. Its unique properties and versatility make it a valuable compound in the development of new pharmaceuticals and fine chemicals.
Used in Organic Chemical Synthesis:
Benzyl acetoacetate serves as a chemical intermediate used for the syntheses of different organic chemicals, as detailed in the product data sheet. Its ability to undergo various chemical reactions and transformations makes it an essential component in the creation of a wide range of organic compounds.

Preparation

By heating ethyl acetoacetate and benzyl alcohol to 160°C.

Purification Methods

Fractionate the ester and collect fractions with the expected physical properties. Otherwise add ca 10% by weight of benzyl alcohol and heat in an oil bath (160-170o, open vessel) for 30minutes during which time excess of benzyl alcohol will have distilled off, then fractionate. [Baker et al. J Org Chem 17 77 1952, Beilstein 6 IV 2480.]

Check Digit Verification of cas no

The CAS Registry Mumber 5396-89-4 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 5,3,9 and 6 respectively; the second part has 2 digits, 8 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 5396-89:
(6*5)+(5*3)+(4*9)+(3*6)+(2*8)+(1*9)=124
124 % 10 = 4
So 5396-89-4 is a valid CAS Registry Number.
InChI:InChI=1/C11H12O3/c1-9(12)7-11(13)14-8-10-5-3-2-4-6-10/h2-6H,7-8H2,1H3

5396-89-4 Well-known Company Product Price

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  • TCI America

  • (A1080)  Benzyl Acetoacetate  >95.0%(GC)

  • 5396-89-4

  • 25mL

  • 225.00CNY

  • Detail
  • TCI America

  • (A1080)  Benzyl Acetoacetate  >95.0%(GC)

  • 5396-89-4

  • 100mL

  • 615.00CNY

  • Detail
  • TCI America

  • (A1080)  Benzyl Acetoacetate  >95.0%(GC)

  • 5396-89-4

  • 500mL

  • 1,930.00CNY

  • Detail
  • Alfa Aesar

  • (A14915)  Benzyl acetoacetate, 97%   

  • 5396-89-4

  • 25g

  • 194.0CNY

  • Detail
  • Alfa Aesar

  • (A14915)  Benzyl acetoacetate, 97%   

  • 5396-89-4

  • 50g

  • 353.0CNY

  • Detail
  • Alfa Aesar

  • (A14915)  Benzyl acetoacetate, 97%   

  • 5396-89-4

  • 100g

  • 498.0CNY

  • Detail
  • Alfa Aesar

  • (A14915)  Benzyl acetoacetate, 97%   

  • 5396-89-4

  • 250g

  • 1060.0CNY

  • Detail

5396-89-4SDS

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 BENZYL ACETOACETATE

1.2 Other means of identification

Product number -
Other names FEMA 2136

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Food additives -> Flavoring Agents
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:5396-89-4 SDS

5396-89-4Relevant articles and documents

A simple and efficient preparation of propargylic β-keto esters through transesterification

Mottet,Hamelin,Garavel,Depres,Greene

, p. 1380 - 1382 (1999)

-

Revisiting ageless antiques; synthesis, biological evaluation, docking simulation and mechanistic insights of 1,4-Dihydropyridines as anticancer agents

Sidhom, Peter A.,El-Bastawissy, Eman,Salama, Abeer A.,El-Moselhy, Tarek F.

supporting information, (2021/06/21)

The historic DHP nucleus was serendipitously discovered by Arthur Hantzsch about 130 years ago and is still considered a hidden treasure for various pharmacological activities. Twenty-one DHP analogues were synthesized using the expedient one pot Hantzsch synthesis for screening as anticancer agents. Initially, the in vitro anti-proliferative single dose against a panel of 18 cancer cell lines showed that compounds 11b and 8f were the superlative candidates regarding their antitumor effect (GI% mean = 66.40% and 50.42%, correspondingly) compared to cisplatin (GI% mean = 65.58%) and doxorubicin (GI% mean = 74.56%). Remarkably, compound 11b showed a remarkable MDA-MB-468 anticancer activity (GI%=80.81%), higher than cisplatin (64.44%) and doxorubicin (76.72%), as well as strong antitumor activity against lung cancer A549 (GI%= 83.02%), more powerful than both cisplatin and doxorubicin. Compound 11b exhibited an exceptional anticancer activity against lung cancer cell line (A549) as its GI50 in nanomolar was (540 nM) with a 9-fold increase greater than cisplatin (GI50 = 4.93 μM) and with a selectivity index = 131 to cancer cells over normal cells. Further mechanistic investigations proved that DHPs anticipate simultaneously TOPI and RTKs (VEGFR-2, HER-2 and BTK) which can stimulate BAX/BAK and the executioner caspases via rtPCR studies.

Design, synthesis, and molecular docking study of new monastrol analogues as kinesin spindle protein inhibitors

El-Hamamsy, Mervat H.,Sharafeldin, Nabaweya A.,El-Moselhy, Tarek F.,Tawfik, Haytham O.

, (2020/06/03)

Lung, colorectal, and breast cancers are the top three types of cancer by incidence and are responsible for one-third of the cancer incidence and mortality. A series of 18 3,4-dihydropyrimidine analogues bearing a 1,2-methylenedioxybenzene component at position 4 with diverse side chains at positions 5 and 6 was designed and synthesized as inhibitors of the Eg5 kinesin enzyme. Target compounds were screened for their anticancer activity according to the NCI-USA protocol toward a panel of 60 cancer cell lines. Compounds 12a and 12b displayed the best antiproliferation activity against many cell lines. Interestingly, compound 12a displayed lethal effects against non-small-cell lung cancer NCI-H522 cells (?42.26%) and MDA-MB-468 breast cancer cells (?1.10%) at a single-dose assay concentration of 10?5 M. Compounds 11c, 11d, 11g, 12a–d, 13, 15, and 18a were assayed against the kinesin enzyme, with IC50 values ranging from 1.2 to 18.71 μM, which were more potent compared with monastrol (IC50 = 20 μM). Cell cycle analysis of NCI-H522 cells treated with compound 12a showed cell cycle arrest at the G2/M phase. Furthermore, the expression levels of active caspase-3 and -9 were measured. A molecular docking study was performed for some demonstrative compounds as well as monastrol docked into the allosteric binding site of the kinesin spindle protein.

Design, synthesis, and bioactivity of dihydropyrimidine derivatives as kinesin spindle protein inhibitors

Tawfik, Haytham O.,El-Hamamsy, Mervat H.,Sharafeldin, Nabaweya A.,El-Moselhy, Tarek F.

, (2019/11/11)

A series of twenty-one 3,4-dihydropyrimidine derivatives bearing the heterocyclic 1,3-benzodioxole at position 4 in addition to different substituents at positions 2, 3 and 5 were designed and synthesized as monastrol analogs. The novel synthesized compounds were screened for their cytotoxic activity towards 60 cancer cell lines according to NCI (USA) protocol. Compounds 10b and 15 showed the best antitumor activity against most cell lines. Compound 15 was subsequently tested in 5-doses mode and displayed high selectivity towards CNS, prostate and leukemia subpanel with selectivity ratios of 22.30, 15.38 and 12.56, respectively at GI50 level. The IC50 of compounds 9d, 10b, 12, 15 and 16 against kinesin enzyme were 3.86 ± 0.12, 10.70 ± 0.35, 3.95 ± 0.12, 4.36 ± 0.14, and 14.07 ± 0.45 μM respectively, while the prototype compound, monastrol, reported IC50 value of 20 ± 0.42 μM. The safest compound among test compounds against normal cell line (HEK 293) is 10b with IC50 value of 62.02 ± 2.42 μM/ml in comparison to doxorubicin (IC50 = 11.34 ± 0.44 μM/ml). Cell cycle analysis of SNB-75 cells treated with compound 15 showed cell cycle arrest at G2/M phase. Further, the assay of levels of active caspase-3 and caspase-9 was investigated. Moreover, Molecular docking of compounds, 9d, 10b, 12, 15, 16, monastrol and mon-97 was performed to study the interaction between inhibitors and the kinesin spindle protein allosteric binding site.

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