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Cerebrosterol
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WARNING: This product is for research use only, not for human or veterinary use.

Hodoodo CAT#: H563744

CAS#: 474-73-7

Description: Cerebrosterol is a major brain metabolite of cholesterol.

Chemical Structure

Cerebrosterol

CAS# 474-73-7

Instruction

Theoretical Analysis

Hodoodo Cat#: H563744
Name: Cerebrosterol
CAS#: 474-73-7
Chemical Formula: C27H46O2
Exact Mass: 402.35
Molecular Weight: 402.660
Elemental Analysis: C, 80.54; H, 11.52; O, 7.95

Price and Availability

Size	Price	Availability
5mg	USD 495	2 Weeks
10mg	USD 895	2 Weeks
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. Hodoodo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

Synonym: Cerebrosterol; 24(S)-hydroxy Cholesterol;

IUPAC/Chemical Name: (3S,4S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-((R)-6-methylheptan-2-yl)-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-3,4-diol

InChi Key: CZDKQKOAHAICSF-GFYXKKFXSA-N

InChi Code: InChI=1S/C27H46O2/c1-17(2)7-6-8-18(3)20-11-12-21-19-9-10-23-25(29)24(28)14-16-27(23,5)22(19)13-15-26(20,21)4/h10,17-22,24-25,28-29H,6-9,11-16H2,1-5H3/t18-,19+,20-,21+,22+,24+,25+,26-,27-/m1/s1

SMILES Code: CC(C)CCC[C@@H](C)[C@H]1CC[C@@]2([H])[C@]3([H])CC=C4[C@H](O)[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >3 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.03.00

More Info:

Instruction:

View handling instruction

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 402.66 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:
In vitro protocol:
In vivo protocol:

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1: Taubert A, Silva LMR, Velásquez ZD, Larrazabal C, Lütjohann D, Hermosilla C. Modulation of cholesterol-related sterols during Eimeria bovis macromeront formation and impact of selected oxysterols on parasite development. Mol Biochem Parasitol. 2018 Jul;223:1-12. doi: 10.1016/j.molbiopara.2018.06.002. Epub 2018 Jun 15. PubMed PMID: 29909067.

2: Lin JB, Sene A, Santeford A, Fujiwara H, Sidhu R, Ligon MM, Shankar VA, Ban N, Mysorekar IU, Ory DS, Apte RS. Oxysterol Signatures Distinguish Age-Related Macular Degeneration from Physiologic Aging. EBioMedicine. 2018 Jun;32:9-20. doi: 10.1016/j.ebiom.2018.05.035. Epub 2018 Jun 11. PubMed PMID: 29903570; PubMed Central PMCID: PMC6021272.

3: Testa G, Staurenghi E, Giannelli S, Gargiulo S, Guglielmotto M, Tabaton M, Tamagno E, Gamba P, Leonarduzzi G. A silver lining for 24-hydroxycholesterol in Alzheimer's disease: The involvement of the neuroprotective enzyme sirtuin 1. Redox Biol. 2018 Jul;17:423-431. doi: 10.1016/j.redox.2018.05.009. Epub 2018 May 22. PubMed PMID: 29883958; PubMed Central PMCID: PMC6007083.

4: Grayaa S, Zerbinati C, Messedi M, HadjKacem I, Chtourou M, Ben Touhemi D, Naifar M, Ayadi H, Ayedi F, Iuliano L. Plasma oxysterol profiling in children reveals 24-hydroxycholesterol as a potential marker for Autism Spectrum Disorders. Biochimie. 2018 May 4. pii: S0300-9084(18)30122-6. doi: 10.1016/j.biochi.2018.04.026. [Epub ahead of print] PubMed PMID: 29730299.

5: Nunes VS, Cazita PM, Catanozi S, Nakandakare ER, Quintão ECR. Decreased content, rate of synthesis and export of cholesterol in the brain of apoE knockout mice. J Bioenerg Biomembr. 2018 Aug;50(4):283-287. doi: 10.1007/s10863-018-9757-9. Epub 2018 Apr 20. PubMed PMID: 29675736.

6: Di Natale C, Monaco A, Pedone C, Tessitore A, De Mase A, Tedeschi G, Netti PA, Abrescia P. The level of 24-hydroxycholesteryl esters decreases in plasma of patients with Parkinson's disease. Neurosci Lett. 2018 Apr 13;672:108-112. doi: 10.1016/j.neulet.2018.02.041. Epub 2018 Feb 24. PubMed PMID: 29486288.

7: Navarro-Mabarak C, Camacho-Carranza R, Espinosa-Aguirre JJ. Cytochrome P450 in the central nervous system as a therapeutic target in neurodegenerative diseases. Drug Metab Rev. 2018 May;50(2):95-108. doi: 10.1080/03602532.2018.1439502. Epub 2018 Feb 16. PubMed PMID: 29451034.

8: Mendiara I, Domeño C, Nerín C, Geurts AM, Osada J, Martínez-Beamonte R. Determination of total plasma oxysterols by enzymatic hydrolysis, solid phase extraction and liquid chromatography coupled to mass-spectrometry. J Pharm Biomed Anal. 2018 Feb 20;150:396-405. doi: 10.1016/j.jpba.2017.12.033. Epub 2017 Dec 21. PubMed PMID: 29288965.

9: Zhang X, Lv C, An Y, Liu Q, Rong H, Tao L, Wang Y, Wang Y, Xiao R. Increased Levels of 27-Hydroxycholesterol Induced by Dietary Cholesterol in Brain Contribute to Learning and Memory Impairment in Rats. Mol Nutr Food Res. 2018 Feb;62(3). doi: 10.1002/mnfr.201700531. Epub 2018 Jan 2. PubMed PMID: 29193679.

10: Dumolt JH, Radhakrishnan SK, Moghadasian MH, Le K, Patel MS, Browne RW, Rideout TC. Maternal hypercholesterolemia enhances oxysterol concentration in mothers and newly weaned offspring but is attenuated by maternal phytosterol supplementation. J Nutr Biochem. 2018 Feb;52:10-17. doi: 10.1016/j.jnutbio.2017.09.013. Epub 2017 Sep 28. PubMed PMID: 29107136.

11: Mast N, Lin JB, Anderson KW, Bjorkhem I, Pikuleva IA. Transcriptional and post-translational changes in the brain of mice deficient in cholesterol removal mediated by cytochrome P450 46A1 (CYP46A1). PLoS One. 2017 Oct 26;12(10):e0187168. doi: 10.1371/journal.pone.0187168. eCollection 2017. Erratum in: PLoS One. 2018 Jan 5;13(1):e0191058. PubMed PMID: 29073233; PubMed Central PMCID: PMC5658173.

12: Mast N, Saadane A, Valencia-Olvera A, Constans J, Maxfield E, Arakawa H, Li Y, Landreth G, Pikuleva IA. Cholesterol-metabolizing enzyme cytochrome P450 46A1 as a pharmacologic target for Alzheimer's disease. Neuropharmacology. 2017 Sep 1;123:465-476. doi: 10.1016/j.neuropharm.2017.06.026. Epub 2017 Jun 24. PubMed PMID: 28655608; PubMed Central PMCID: PMC5546235.

13: Gambert S, Gabrielle PH, Masson E, Leger-Charnay E, Ferrerro A, Vannier A, Gendrault C, Lachot M, Creuzot-Garcher C, Bron A, Gregoire S, Leclere L, Martine L, Lucchi G, Truntzer C, Pecqueur D, Bretillon L. Cholesterol metabolism and glaucoma: Modulation of Muller cell membrane organization by 24S-hydroxycholesterol. Chem Phys Lipids. 2017 Oct;207(Pt B):179-191. doi: 10.1016/j.chemphyslip.2017.05.007. Epub 2017 Jun 4. PubMed PMID: 28576383.

14: Sun MY, Taylor A, Zorumski CF, Mennerick S. 24S-hydroxycholesterol and 25-hydroxycholesterol differentially impact hippocampal neuronal survival following oxygen-glucose deprivation. PLoS One. 2017 Mar 27;12(3):e0174416. doi: 10.1371/journal.pone.0174416. eCollection 2017. PubMed PMID: 28346482; PubMed Central PMCID: PMC5367825.

15: Šošić-Jurjević B, Lütjohann D, Jarić I, Miler M, Vojnović Milutinović D, Filipović B, Ajdžanović V, Renko K, Wirth EK, Janković S, Kӧhrle J, Milošević V. Effects of age and soybean isoflavones on hepatic cholesterol metabolism and thyroid hormone availability in acyclic female rats. Exp Gerontol. 2017 Jun;92:74-81. doi: 10.1016/j.exger.2017.03.016. Epub 2017 Mar 21. PubMed PMID: 28336316.

16: Bezine M, Debbabi M, Nury T, Ben-Khalifa R, Samadi M, Cherkaoui-Malki M, Vejux A, Raas Q, de Sèze J, Moreau T, El-Ayeb M, Lizard G. Evidence of K(+) homeostasis disruption in cellular dysfunction triggered by 7-ketocholesterol, 24S-hydroxycholesterol, and tetracosanoic acid (C24:0) in 158N murine oligodendrocytes. Chem Phys Lipids. 2017 Oct;207(Pt B):135-150. doi: 10.1016/j.chemphyslip.2017.03.006. Epub 2017 Mar 18. PubMed PMID: 28322741.

17: Kasimov MR, Fatkhrakhmanova MR, Mukhutdinova KA, Petrov AM. 24S-Hydroxycholesterol enhances synaptic vesicle cycling in the mouse neuromuscular junction: Implication of glutamate NMDA receptors and nitric oxide. Neuropharmacology. 2017 May 1;117:61-73. doi: 10.1016/j.neuropharm.2017.01.030. Epub 2017 Jan 31. PubMed PMID: 28153530.

18: Liu Q, An Y, Yu H, Lu Y, Feng L, Wang C, Xiao R. Relationship between oxysterols and mild cognitive impairment in the elderly: a case-control study. Lipids Health Dis. 2016 Oct 10;15(1):177. PubMed PMID: 27724967; PubMed Central PMCID: PMC5057217.

19: Testa G, Staurenghi E, Zerbinati C, Gargiulo S, Iuliano L, Giaccone G, Fantò F, Poli G, Leonarduzzi G, Gamba P. Changes in brain oxysterols at different stages of Alzheimer's disease: Their involvement in neuroinflammation. Redox Biol. 2016 Dec;10:24-33. doi: 10.1016/j.redox.2016.09.001. Epub 2016 Sep 16. PubMed PMID: 27687218; PubMed Central PMCID: PMC5040635.

20: Soncini M, Corna G, Moresco M, Coltella N, Restuccia U, Maggioni D, Raccosta L, Lin CY, Invernizzi F, Crocchiolo R, Doglioni C, Traversari C, Bachi A, Bernardi R, Bordignon C, Gustafsson JÅ, Russo V. 24-Hydroxycholesterol participates in pancreatic neuroendocrine tumor development. Proc Natl Acad Sci U S A. 2016 Oct 11;113(41):E6219-E6227. Epub 2016 Sep 26. PubMed PMID: 27671648; PubMed Central PMCID: PMC5068323.

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