Benzylideneacetone
(Synonyms: 苄叉丙酮,Benzalacetone) 目录号 : GC60640
Benzylideneacetone是一种内源性代谢产物。
Cas No.:122-57-6
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >98.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Benzylideneacetone is an endogenous metabolite.
| Cas No. | 122-57-6 | SDF | |
| 别名 | 苄叉丙酮,Benzalacetone | ||
| Canonical SMILES | CC(/C=C/C1=CC=CC=C1)=O | ||
| 分子式 | C10H10O | 分子量 | 146.19 |
| 溶解度 | 储存条件 | Store at -20°C | |
| General tips | 请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液；一旦配成溶液，请分装保存，避免反复冻融造成的产品失效。 储备液的保存方式和期限：-80°C 储存时，请在 6 个月内使用，-20°C 储存时，请在 1 个月内使用。 为了提高溶解度，请将管子加热至37℃，然后在超声波浴中震荡一段时间。 |
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| Shipping Condition | 评估样品解决方案：配备蓝冰进行发货。所有其他可用尺寸：配备RT，或根据请求配备蓝冰。 | ||
| 制备储备液 | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 6.8404 mL | 34.2021 mL | 68.4041 mL |
| 5 mM | 1.3681 mL | 6.8404 mL | 13.6808 mL |
| 10 mM | 0.684 mL | 3.4202 mL | 6.8404 mL |
| 第一步：请输入基本实验信息（考虑到实验过程中的损耗，建议多配一只动物的药量） | ||||||||||
| 给药剂量 | mg/kg |  |
动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
| 第二步：请输入动物体内配方组成（配方适用于不溶于水的药物；不同批次药物配方比例不同，请联系GLPBIO为您提供正确的澄清溶液配方） | ||||||||||
| % DMSO % % Tween 80 % saline | ||||||||||
| 计算重置 | ||||||||||
计算结果:
工作液浓度： mg/ml；
DMSO母液配制方法： mg 药物溶于 μL DMSO溶液（母液浓度 mg/mL，
体内配方配制方法：取 μL DMSO母液，加入 μL PEG300，混匀澄清后加入μL Tween 80，混匀澄清后加入 μL saline，混匀澄清。
1. 首先保证母液是澄清的；
2.
一定要按照顺序依次将溶剂加入，进行下一步操作之前必须保证上一步操作得到的是澄清的溶液，可采用涡旋、超声或水浴加热等物理方法助溶。
3. 以上所有助溶剂都可在 GlpBio 网站选购。
Benzylideneacetone Derivatives Inhibit Osteoclastogenesis and Activate Osteoblastogenesis Independently Based on Specific Structure-Activity Relationship
J Med Chem 2019 Jul 11;62(13):6063-6082.PMID:31257875DOI:10.1021/acs.jmedchem.9b00270.
(E)-3,4-Dihydroxybenzylideneacetone (compound 1) inhibited receptor activator of NF-κB ligand-induced osteoclastogenesis of C57BL/6 bone marrow monocyte/macrophages with IC50 of 7.8 μM (IC50 of alendronate, 3.7 μM) while stimulating the differentiation of MC3T3-E1 osteoblastic cells, accompanied by the induction of Runt-related transcription factor 2, alkaline phosphatase, and osteocalcin. (E)-4-(3-Hydroxy-4-methoxyphenyl)-3-buten-2-one (compound 2c) showed a dramatically increased osteoclast-inhibitory potency with IC50 of 0.11 μM while sustaining osteoblast-stimulatory activity. (E)-4-(4-Hydroxy-3-methoxyphenyl)-3-buten-2-one (compound 2g) stimulated alkaline phosphatase production 2-fold at 50 μM without changing osteoclast-inhibitory activity, compared with compound 1. Oral administration of compounds 1, 2c, and 2g prevented ovariectomy-induced osteoporosis in ddY mice to a degree proportional to their osteoclastogenesis-inhibitory potencies. The administration of 1 (mg/kg)/d compound 2c ameliorated histomorphometry of osteoporotic bone to a degree comparable with 10 (mg/kg)/d alendronate. Conclusively, the in vitro capacity of a few Benzylideneacetone derivatives to inhibit osteoclastogenesis supported by independent osteoblastogenesis activation was convincingly reflected in in vivo management of osteoporosis, suggesting a potential novel therapeutics for osteopenic diseases.
Inhibition effects of Benzylideneacetone, benzylacetone, and 4-phenyl-2-butanol on the activity of mushroom tyrosinase
J Biosci Bioeng 2015 Mar;119(3):275-9.PMID:25441446DOI:10.1016/j.jbiosc.2014.08.014.
Tyrosinase (EC 1.14.18.1) is the key enzyme of melanin synthesis and fruit-vegetable browning. The inhibition of Benzylideneacetone, benzylacetone, and 4-phenyl-2-butanol on mushroom tyrosinase was first investigated. The results shown that these three compounds could effectively inhibit the enzyme activity sharply and the inhibitory effects were determined to be reversible. Their inhibitor concentrations leading to 50% activity lost values were determined to be 1.5, 2.8, and 1.1 mM for monophenolase and 2.0, 0.6, and 0.8 mM for diphenolase, respectively. For the monophenolase activity, all of these three compounds were mixed-type inhibitors, however, only 4-phenyl-2-butanol obviously lengthened the lag time. For the diphenolase activity, Benzylideneacetone and benzylacetone were mixed-type inhibitors, while 4-phenyl-2-butanol was a noncompetitive type inhibitor. In conclusion, these compounds exhibited potent antityrosinase activities. This research would provide scientific evidence for the use of Benzylideneacetone, benzylacetone, and 4-phenyl-2-butanol as antityrosinase agents.
Benzylideneacetone, an eicosanoid biosynthesis inhibitor enhances baculovirus pathogenicity in the diamondback moth, Plutella xylostella
J Invertebr Pathol 2011 Feb;106(2):308-13.PMID:21112333DOI:10.1016/j.jip.2010.11.006.
Benzylideneacetone (BZA) is a monoterpenoid compound produced by an entomopathogenic bacterium, Xenorhabdus nematophila. BZA inhibits phospholipase A(2) to suppress biosynthesis of eicosanoids that mediate immune responses in insects. In response to per os infection of Autographa californica multiple nucleopolyhedrosis virus (AcMNPV), the diamondback moth, Plutella xylostella, developed red spots on the midgut epithelium. The midgut exhibiting red spot formation suffered abnormal cell integrity, such as genomic DNA fragmentation and condensed spots in the nucleoplasm. The number of red spots increased with viral dose and incubation time after the viral treatment. BZA inhibited the formation of the midgut red spots in a dose-dependent manner. However, the inhibitory effect of BZA on the red spot formation was reversed by addition of arachidonic acid, suggesting that the red spot response may be mediated by eicosanoids. BZA treatment resulted in significant enhancement of AcMNPV occlusion body (OB) pathogenicity to P. xylostella.
Benzylideneacetone, an immunosuppressant, enhances virulence of Bacillus thuringiensis against beet armyworm (Lepidoptera: Noctuidae)
J Econ Entomol 2008 Feb;101(1):36-41.PMID:18330113DOI:10.1603/0022-0493(2008)101[36:baievo]2.0.co;2.
Benzylideneacetone (BZA) is a metabolite of gram-negative entomopathogenic bacterium Xenorhabdus nematophila, and it acts as an enzyme inhibitor against phospholipase A2 (PLA2). PLA2 catalyzes a committed biosynthetic step of eicosanoids, which mediate insect immune reactions to infection by microbial pathogens. This study tested a hypothesis that a putative immunosuppressive activity of BZA may enhance virulence of Bacillus thuringiensis against the fifth instars of Spodoptera exigua (Hübner) (Lepidoptera: Noctuidae). In in vitro conditions, BZA significantly inhibited hemocyte microaggregation induced by B. thuringiensis and impaired hemocyte-spreading behavior of S. exigua in a dose-dependent manner. Oral administration of BZA gave similar immunosuppressive effect on the hemocytes of the fifth instars. Although BZA itself did not possess any insecticidal activity on oral administration, when BZA was treated in a mixture with a low dose of B. thuringiensis spp. aizawai to fifth instars, the bacterial virulence was significantly enhanced. BZA also enhanced virulence of B. thuringiensis spp. kurstaki, which alone was of limited effectiveness against S. exigua. This study suggests that an immunosuppression by BZA is positively linked to potentiation of B. thuringiensis.
Additive-assisted regioselective 1,3-dipolar cycloaddition of azomethine ylides with Benzylideneacetone
Beilstein J Org Chem 2014 Feb 7;10:352-60.PMID:24605156DOI:10.3762/bjoc.10.33.
1,3-Dipolar cycloadditions of isatins, benzylamine and benzylideneacetones were studied to prepare a series of novel spiropyrrolidine-oxindoles - 4'-acetyl-3',5'-diarylspiro[indoline-3,2'-pyrrolidin]-2-ones and 3'-acetyl-4',5'-diarylspiro[indoline-3,2'-pyrrolidine]-2-ones in good yields of up to 94% and with good regioselectivities. Regioselectivities are reversible by the addition of water or 4-nitrobenzoic acid, respectively. The substituent effects on the regioselectivity were also investigated.