Basic Description

Synonyms	Cholestryl stearate \| Spiro(cyclopenta(7,8)phenanthro(4b,5-b)oxirene-7(3H),2'(3'H)-furan)-10-carboxylic acid, 2,4,4',4a,5',5a,6,6a,8,9,9a,9b,10,11-tetradecahydro-4a,6a-dimethyl-2,5'-dioxo-, methyl ester, (4aS,4bR,5aR,6aS,7 R,9aS,9bR,10R)- \| Cholest-5-en-3
Specifications & Purity	≥97%
Shipped In	Normal
Product Description	Cholesteryl stearate is a stearic acid ester of cholesterol. In solid-state, its autoxidation is higher than its free form

Names and Identifiers

IUPAC Name	[(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] octadecanoate
INCHI	InChI=1S/C45H80O2/c1-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-25-43(46)47-38-30-32-44(5)37(34-38)26-27-39-41-29-28-40(36(4)24-22-23-35(2)3)45(41,6)33-31-42(39)44/h26,35-36,38-42H,7-25,27-34H2,1-6H3/t36-,38+,39+,40-,41+,42+,44+,45-/m1/s1
InChi Key	XHRPOTDGOASDJS-XNTGVSEISA-N
Canonical SMILES	CCCCCCCCCCCCCCCCCC(=O)OC1CCC2(C3CCC4(C(C3CC=C2C1)CCC4C(C)CCCC(C)C)C)C
Isomeric SMILES	CCCCCCCCCCCCCCCCCC(=O)O[C@H]1CC[C@@]2([C@H]3CC[C@]4([C@H]([C@@H]3CC=C2C1)CC[C@@H]4[C@H](C)CCCC(C)C)C)C
WGK Germany	3
PubChem CID	118246
Molecular Weight	653.12
Beilstein	2068492

Certificates

Certificate of Analysis(COA)

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7 results found

Lot Number	Certificate Type	Date	Item
H2316327	Certificate of Analysis	Jul 27, 2023	C113862
H2316328	Certificate of Analysis	Jul 27, 2023	C113862
H2316329	Certificate of Analysis	Jul 27, 2023	C113862
H2316330	Certificate of Analysis	Jul 27, 2023	C113862
H2316331	Certificate of Analysis	Jul 27, 2023	C113862
C2201011	Certificate of Analysis	Mar 10, 2022	C113862
E2310090	Certificate of Analysis	Mar 10, 2022	C113862

Chemical and Physical Properties

Solubility	Insoluble in water.
Specific Rotation[α]	-23 ° (C=2, CHCl3)
Melt Point(°C)	79-83°C

Safety and Hazards(GHS)

WGK Germany	3

References

1. Michael A Jansen,Jacqueline Kiwata,Jennifer Arceo,Kym F Faull,Grady Hanrahan,Edith Porter. (2010-05-22) Evolving neural network optimization of cholesteryl ester separation by reversed-phase HPLC.. Analytical and bioanalytical chemistry, 397 ((6)): (2367-2374). [PMID:20490467]
2. Cristina P Almeida,Carolina G Vital,Thais C Contente,Durvanei A Maria,Raul C Maranhão. (2010-10-20) Modification of composition of a nanoemulsion with different cholesteryl ester molecular species: effects on stability, peroxidation, and cell uptake.. International journal of nanomedicine, 5 (679-686). [PMID:20957219]
3. Petra C Kienesberger,Thomas Pulinilkunnil,Miranda M Y Sung,Jeevan Nagendran,Guenter Haemmerle,Erin E Kershaw,Martin E Young,Peter E Light,Gavin Y Oudit,Rudolf Zechner,Jason R B Dyck. (2011-12-14) Myocardial ATGL overexpression decreases the reliance on fatty acid oxidation and protects against pressure overload-induced cardiac dysfunction.. Molecular and cellular biology, 32 ((4)): (740-750). [PMID:22158969]
4. Emmanuelle Girard,Jean Louis Paul,Natalie Fournier,Philippe Beaune,Ludger Johannes,Christophe Lamaze,Benoît Védie. (2011-12-30) The dynamin chemical inhibitor dynasore impairs cholesterol trafficking and sterol-sensitive genes transcription in human HeLa cells and macrophages.. PloS one, 6 ((12)): (e29042-e29042). [PMID:22205993]
5. Sare Andalib,Jaleh Varshosaz,Farshid Hassanzadeh,Hojjat Sadeghi. (2013-01-18) Optimization of LDL targeted nanostructured lipid carriers of 5-FU by a full factorial design.. Advanced biomedical research, 1 (45-45). [PMID:23326776]
6. Songlin Yu,Jun Dong,Weiyan Zhou,Ruiyue Yang,Hongxia Li,Haijian Zhao,Tianjiao Zhang,Hanbang Guo,Shu Wang,Chuanbao Zhang,Wenxiang Chen. (2014-05-14) A rapid and precise method for quantification of fatty acids in human serum cholesteryl esters by liquid chromatography and tandem mass spectrometry.. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences, 960 (222-229). [PMID:24820975]
7. Simon Hammann,Michael Englert,Marco Müller,Walter Vetter. (2015-10-07) Accelerated separation of GC-amenable lipid classes in plant oils by countercurrent chromatography in the co-current mode.. Analytical and bioanalytical chemistry, 407 ((30)): (9019-9028). [PMID:26438473]
8. Vít Kosek,Milena Stránská,Marie Fenclová,Tomáš Ruml,Libor Vítek,Jana Hajšlová. (2017-02-18) High resolution mass spectrometry based method applicable for a wide range of 3-hydroxy-3-methyl-glutaryl-coenzyme A reductase inhibitors in blood serum including intermediates and products of the cholesterol biosynthetic pathway.. Journal of chromatography. A, 1489 (86-94). [PMID:28209347]
9. Paola Donato,Giuseppe Micalizzi,Marianna Oteri,Francesca Rigano,Danilo Sciarrone,Paola Dugo,Luigi Mondello. (2018-04-19) Comprehensive lipid profiling in the Mediterranean mussel (Mytilus galloprovincialis) using hyphenated and multidimensional chromatography techniques coupled to mass spectrometry detection.. Analytical and bioanalytical chemistry, 410 ((14)): (3297-3313). [PMID:29666913]
10. Clara Barba Albanell,Victor Carrer,Meritxell Marti,Jordi Iglesias,Joan Iglesias,Luisa Coderch. (2018-05-10) Solvent-Extracted Wool Wax: Thermotropic Properties and Skin Efficacy.. Skin pharmacology and physiology, 31 ((4)): (198-205). [PMID:29742517]
11. Sarah E Hancock,Alan T Maccarone,Berwyck L J Poad,Adam J Trevitt,Todd W Mitchell,Stephen J Blanksby. (2019-01-01) Reaction of ionised steryl esters with ozone in the gas phase.. Chemistry and physics of lipids, 221 (198-206). [PMID:30597129]
12. Maciej Roman,Tomasz P Wrobel,Czeslawa Paluszkiewicz,Wojciech M Kwiatek. (2020-01-31) Comparison between high definition FT-IR, Raman and AFM-IR for subcellular chemical imaging of cholesteryl esters in prostate cancer cells.. Journal of biophotonics, 13 ((5)): (e201960094-e201960094). [PMID:31999078]
13. Henry West,Gavin E Reid. (2020-11-30) Hybrid 213\xa0nm photodissociation of cationized Sterol lipid ions yield [M]+. Radical products for improved structural characterization using multistage tandem mass spectrometry.. Analytica chimica acta, 1141 (100-109). [PMID:33248642]
14. Laura Carreón-Palau,Nurgül Şen Özdemir,Christopher C Parrish,Camilla Parzanini. (2020-12-03) Sterol Composition of Sponges, Cnidarians, Arthropods, Mollusks, and Echinoderms from the Deep Northwest Atlantic: A Comparison with Shallow Coastal Gulf of Mexico.. Marine drugs, 18 ((12)): [PMID:33260983]
15. M Cabeza,R Miranda. (1997-01-01) Increased synthesis of cholesterol stearate in flanking organ from gonadectomized female hamsters treated with progesterone and 5 alpha-dihydroprogesterone.. Proceedings of the Western Pharmacology Society, 40 (87-89). [PMID:9436221]
16. J Robin Harris,Sucharit Bhakdi,Ulrich Meissner,Dirk Scheffler,Robert Bittman,Guoqing Li,Alexander Zitzer,Michael Palmer. (2002-10-31) Interaction of the Vibrio cholerae cytolysin (VCC) with cholesterol, some cholesterol esters, and cholesterol derivatives: a TEM study.. Journal of structural biology, 139 ((2)): (122-135). [PMID:12406694]
17. Masayuki Kyomoto,Toru Moro,Shihori Yamane,Yoshio Takatori,Sakae Tanaka,Kazuhiko Ishihara. (2016-10-21) A hydrated phospholipid polymer-grafted layer prevents lipid-related oxidative degradation of cross-linked polyethylene.. Biomaterials, 112 (122-132). [PMID:27760396]
18. Haiyang Feng,Yuping Zhu,Zhixuan Fu,Dechuan Li. (2017-04-23) Preparation, characterization, and in vivo study of rhein solid lipid nanoparticles for oral delivery.. Chemical biology & drug design, 90 ((5)): (867-872). [PMID:28432812]
19. Xiaoyang Sun,Lifen Zhang,Jingfeng Yan,Fanfan Song,Shaojun Tian,Jianchun Xie. (2020-08-14) Effects of enzymatic free fatty acid reduction process on the composition and phytochemicals of rice bran oil.. Food chemistry, 337 (127757-127757). [PMID:32791430]

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SKU	Size	Availability	Price
C113862-5g	5g	Available within 4-8 weeks(?) Items will be manufactured post-order and can take 4-8 weeks. Thank you for your patience!	$70.90
C113862-25g	25g	In stock	$215.90
C113862-100g	100g	In stock	$776.90

Cholesteryl stearate - ≥97.0%, high purity , CAS No.35602-69-8