Basic Description

Synonyms	Cholesteryl hemisuccinate \| 1510-21-0 \| Cholesterol Hydrogen Succinate \| Cholesteryl succinate \| Cholesterol hemisuccinate \| CHEMS \| Cholesteryl hydrogen succinate \| Cholest-5-en-3beta-yl hydrogen succinate \| Cholest-5-en-3-ol (3beta)-, 3-(hydrogen butanedioate) \| 4-[[(3S,
Specifications & Purity	≥97.0%
Shipped In	Normal
Product Description	Cholesteryl hemisuccinate (CHEMS) is an acidic cholesterol ester. It self assembles into bilayers in alkaline and neutral aqueous media. CHEMS exhibits pH sensitive polymorphism. It consists of succinic acid esterified to the beta-hydroxyl group of cholesterol. This chemical modification results in the ability of CHEMS to adopt a lamellar assembly in suitable aqueous media, whereas cholesterol forms monohydrate crystals in an aqueous environment.

Names and Identifiers

Pubchem Sid	488183659
IUPAC Name	4-[[(3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]-4-oxobutanoic acid
INCHI	InChI=1S/C31H50O4/c1-20(2)7-6-8-21(3)25-11-12-26-24-10-9-22-19-23(35-29(34)14-13-28(32)33)15-17-30(22,4)27(24)16-18-31(25,26)5/h9,20-21,23-27H,6-8,10-19H2,1-5H3,(H,32,33)/t21-,23+,24+,25-,26+,27+,30+,31-/m1/s1
InChi Key	WLNARFZDISHUGS-MIXBDBMTSA-N
Canonical SMILES	CC(C)CCCC(C)C1CCC2C1(CCC3C2CC=C4C3(CCC(C4)OC(=O)CCC(=O)O)C)C
Isomeric SMILES	C[C@H](CCCC(C)C)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CC=C4[C@@]3(CC[C@@H](C4)OC(=O)CCC(=O)O)C)C
PubChem CID	65082
Molecular Weight	486.74

Certificates

Certificate of Analysis(COA)

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13 results found

Lot Number	Certificate Type	Date	Item
C2222491	Certificate of Analysis	Jan 05, 2024	C132483
C2222501	Certificate of Analysis	Jan 05, 2024	C132483
C2222502	Certificate of Analysis	Jan 05, 2024	C132483
I2104141	Certificate of Analysis	Jun 13, 2023	C132483
I2104145	Certificate of Analysis	Jun 13, 2023	C132483
B2328423	Certificate of Analysis	Feb 02, 2023	C132483
B2328433	Certificate of Analysis	Feb 02, 2023	C132483
B2328434	Certificate of Analysis	Feb 02, 2023	C132483
B2328435	Certificate of Analysis	Feb 02, 2023	C132483
B2328436	Certificate of Analysis	Feb 02, 2023	C132483
B2328437	Certificate of Analysis	Feb 02, 2023	C132483
C2120056	Certificate of Analysis	Jan 11, 2023	C132483
C2120059	Certificate of Analysis	Jan 11, 2023	C132483

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Chemical and Physical Properties

Specific Rotation[α]	-34° (C=2,CHCl3)
Melt Point(°C)	178℃

Citations of This Product

1. Jingjing Chai, Jiawei Hu, Tao Wang, Xing Bao, Jiajie Luan, Yan Wang. (2024) A Multifunctional Liposome for Synergistic Chemotherapy with Ferroptosis Activation of Triple-Negative Breast Cancer. MOLECULAR PHARMACEUTICS, 21 (2): (781–790). [PMID:38153044]
2. Pengyu Li, Jieyi Pan, Yating Dong, Yingying Sun, Yalong Wang, Kang Liao, Yili Chen, Xin Deng, Shihui Yu, Haiyan Hu. (2024) Microenvironment responsive charge-switchable nanoparticles act on biofilm eradication and virulence inhibition for chronic lung infection treatment. JOURNAL OF CONTROLLED RELEASE, 365 (4): (219). [PMID:37992874]
3. Di Chuan, Rangrang Fan, Bo Chen, Yangmei Ren, Min Mu, Haifeng Chen, Bingwen Zou, Haohao Dong, Aiping Tong, Gang Guo. (2023) Lipid–Polymer Hybrid Nanoparticles with Both PD-L1 Knockdown and Mild Photothermal Effect for Tumor Photothermal Immunotherapy. ACS Applied Materials & Interfaces, [PMID:37605506]
4. Yuan Lin, Yimin Zhang, Zhuang Xiong, Min Wu, Muling Zeng, Chuangnan Li, Fujin Liu, Yazhi Liao, Chunping Liu, Jing Chen. (2023) Development of glycyrrhetinic acid ligand-functionalized liposomes for targeting hepatocellular carcinoma: Synthesis, preparation, characterization, and evaluation. Arabian Journal of Chemistry, 16 (105131). [PMID:]
5. Mengjun Zhang, Huiyang Jiang, Lan Wu, Haoyu Lu, Hriday Bera, Xing Zhao, Xiong Guo, Xulu Liu, Dongmei Cun, Mingshi Yang. (2022) Airway epithelial cell-specific delivery of lipid nanoparticles loading siRNA for asthma treatment. JOURNAL OF CONTROLLED RELEASE, 352 (422). [PMID:36265740]
6. Lina Zhang, Yutao Jia, Han Hao, Mi Wang, Jing Wang. (2022) Mitochondria-targeted liposome-enveloped covalent organic framework co-delivery system for enhanced tumor therapy. MICROPOROUS AND MESOPOROUS MATERIALS, 344 (112198). [PMID:]
7. Taiying Chen, Ngalei Tam, Yu Mao, Chengjun Sun, Zekang Wang, Yuchen Hou, Wuzheng Xia, Jia Yu, Linwei Wu. (2022) A multi-hit therapeutic nanoplatform for hepatocellular carcinoma: Dual stimuli-responsive drug release, dual-modal imaging, and in situ oxygen supply to enhance synergistic therapy. Materials Today Bio, 16 (100338). [PMID:35847375]
8. Miaomiao Qi, Xiang Liu, Ying Zhou, Haoyu Wang, Ying Zhao, Jing Ren, Jin Xiang. (2021) Berberine Inhibits MDA-MB-231 Cells as an Agonist of G Protein-Coupled Estrogen Receptor 1. INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES, 22 (21): (11466). [PMID:34768896]

References

1. Jingjing Chai, Jiawei Hu, Tao Wang, Xing Bao, Jiajie Luan, Yan Wang. (2024) A Multifunctional Liposome for Synergistic Chemotherapy with Ferroptosis Activation of Triple-Negative Breast Cancer. MOLECULAR PHARMACEUTICS, 21 (2): (781–790). [PMID:38153044]
2. Pengyu Li, Jieyi Pan, Yating Dong, Yingying Sun, Yalong Wang, Kang Liao, Yili Chen, Xin Deng, Shihui Yu, Haiyan Hu. (2024) Microenvironment responsive charge-switchable nanoparticles act on biofilm eradication and virulence inhibition for chronic lung infection treatment. JOURNAL OF CONTROLLED RELEASE, 365 (4): (219). [PMID:37992874]
3. Di Chuan, Rangrang Fan, Bo Chen, Yangmei Ren, Min Mu, Haifeng Chen, Bingwen Zou, Haohao Dong, Aiping Tong, Gang Guo. (2023) Lipid–Polymer Hybrid Nanoparticles with Both PD-L1 Knockdown and Mild Photothermal Effect for Tumor Photothermal Immunotherapy. ACS Applied Materials & Interfaces, [PMID:37605506]
4. Yuan Lin, Yimin Zhang, Zhuang Xiong, Min Wu, Muling Zeng, Chuangnan Li, Fujin Liu, Yazhi Liao, Chunping Liu, Jing Chen. (2023) Development of glycyrrhetinic acid ligand-functionalized liposomes for targeting hepatocellular carcinoma: Synthesis, preparation, characterization, and evaluation. Arabian Journal of Chemistry, 16 (105131). [PMID:]
5. Mengjun Zhang, Huiyang Jiang, Lan Wu, Haoyu Lu, Hriday Bera, Xing Zhao, Xiong Guo, Xulu Liu, Dongmei Cun, Mingshi Yang. (2022) Airway epithelial cell-specific delivery of lipid nanoparticles loading siRNA for asthma treatment. JOURNAL OF CONTROLLED RELEASE, 352 (422). [PMID:36265740]
6. Lina Zhang, Yutao Jia, Han Hao, Mi Wang, Jing Wang. (2022) Mitochondria-targeted liposome-enveloped covalent organic framework co-delivery system for enhanced tumor therapy. MICROPOROUS AND MESOPOROUS MATERIALS, 344 (112198). [PMID:]
7. Taiying Chen, Ngalei Tam, Yu Mao, Chengjun Sun, Zekang Wang, Yuchen Hou, Wuzheng Xia, Jia Yu, Linwei Wu. (2022) A multi-hit therapeutic nanoplatform for hepatocellular carcinoma: Dual stimuli-responsive drug release, dual-modal imaging, and in situ oxygen supply to enhance synergistic therapy. Materials Today Bio, 16 (100338). [PMID:35847375]
8. Miaomiao Qi, Xiang Liu, Ying Zhou, Haoyu Wang, Ying Zhao, Jing Ren, Jin Xiang. (2021) Berberine Inhibits MDA-MB-231 Cells as an Agonist of G Protein-Coupled Estrogen Receptor 1. INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES, 22 (21): (11466). [PMID:34768896]

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SKU	Size	Availability	Price
C132483-1g	1g	In stock	$54.90
C132483-5g	5g	In stock	$208.90
C132483-25g	25g	In stock	$690.90

Cholesteryl hemisuccinate - ≥97.0%, high purity , CAS No.1510-21-0