27-Hydroxycholesterol
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MedKoo CAT#: 526668

CAS#: 20380-11-4

Description: 27-Hydroxycholesterol, also known as 27-HC, is an endogenous oxysterol with multiple biological functions, including activity as a selective estrogen receptor modulator (SERM) (a mixed, tissue-specific agonist-antagonist of the estrogen receptor (ER)) and as an agonist of the liver X receptor (LXR). It is a metabolite of cholesterol that is produced by the enzyme CYP27A1. 27-Hydroxycholesterol suppresses lipid accumulation by down-regulating lipogenic and adipogenic gene expression in 3T3-L1 cells. 27-Hydroxycholesterol stimulates cell proliferation and resistance to docetaxel-induced apoptosis in prostate epithelial cells.


Price and Availability

Size
Price

1g
USD 4650
10g
Ask price
Size
Price

2g
USD 5850
Size
Price

5g
USD 7250

27-Hydroxycholesterol is not in stock, may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 526668
Name: 27-Hydroxycholesterol
CAS#: 20380-11-4
Chemical Formula: C27H46O2
Exact Mass: 402.3498
Molecular Weight: 402.663
Elemental Analysis: C, 80.54; H, 11.52; O, 7.95


Synonym: 27-Hydroxycholesterol, 27-HC.

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

InChi Key: FYHRJWMENCALJY-YSQMORBQSA-N

InChi Code: InChI=1S/C27H46O2/c1-18(17-28)6-5-7-19(2)23-10-11-24-22-9-8-20-16-21(29)12-14-26(20,3)25(22)13-15-27(23,24)4/h8,18-19,21-25,28-29H,5-7,9-17H2,1-4H3/t18-,19-,21+,22+,23-,24+,25+,26+,27-/m1/s1

SMILES Code: C[C@@H](CO)CCC[C@@H](C)[C@H]1CC[C@@]2([H])[C@]3([H])CC=C4C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C


Technical Data

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, not in water

Shelf Life:
>2 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).

Harmonized System Code:
293490


Additional Information

Because of its estrogenic action, 27-HC stimulates the growth of ER-positive breast cancer cells, and has been implicated in limiting the effectiveness of aromatase inhibitors in the treatment of breast cancer. As such, identified CYP27A1 inhibitors, including the marketed drugs anastrozole, fadrozole, bicalutamide, dexmedetomidine, ravuconazole, and posaconazole, have been proposed as potential adjuvant therapies in ER-positive breast cancer.


References

1: Hashimoto Y, Sugiura H, Togo S, Koarai A, Abe K, Yamada M, Ichikawa T, Kikuchi T, Numakura T, Onodera K, Tanaka R, Sato K, Yanagisawa S, Okazaki T, Tamada T, Kikuchi T, Hoshikawa Y, Okada Y, Ichinose M. 27-Hydroxycholesterol accelerates cellular senescence in human lung resident cells. Am J Physiol Lung Cell Mol Physiol. 2016 Jun 1;310(11):L1028-41. doi: 10.1152/ajplung.00351.2015. Epub 2016 Apr 1. PubMed PMID: 27036870.

2: Shirouchi B, Kashima K, Horiuchi Y, Nakamura Y, Fujimoto Y, Tong LT, Sato M. 27-Hydroxycholesterol suppresses lipid accumulation by down-regulating lipogenic and adipogenic gene expression in 3T3-L1 cells. Cytotechnology. 2016 Mar 17. [Epub ahead of print] PubMed PMID: 26983933.

3: Roberg-Larsen H, Lund K, Seterdal KE, Solheim S, Vehus T, Solberg N, Krauss S, Lundanes E, Wilson SR. Mass spectrometric detection of 27-hydroxycholesterol in breast cancer exosomes. J Steroid Biochem Mol Biol. 2016 Feb 10. pii: S0960-0760(16)30020-6. doi: 10.1016/j.jsbmb.2016.02.006. [Epub ahead of print] PubMed PMID: 26877254.

4: Heverin M, Ali Z, Olin M, Tillander V, Joibari MM, Makoveichuk E, Leitersdorf E, Warner M, Olivercrona G, Gustafsson JÅ, Björkhem I. On the regulatory importance of 27-hydroxycholesterol in mouse liver. J Steroid Biochem Mol Biol. 2016 Feb 3. pii: S0960-0760(16)30015-2. doi: 10.1016/j.jsbmb.2016.02.001. [Epub ahead of print] Review. PubMed PMID: 26851362.

5: Wang HL, Wang YY, Liu XG, Kuo SH, Liu N, Song QY, Wang MW. Cholesterol, 24-Hydroxycholesterol, and 27-Hydroxycholesterol as Surrogate Biomarkers in Cerebrospinal Fluid in Mild Cognitive Impairment and Alzheimer's Disease: A Meta-Analysis. J Alzheimers Dis. 2016 Jan 13;51(1):45-55. doi: 10.3233/JAD-150734. PubMed PMID: 26836015.

6: Vini R, Juberiya AM, Sreeja S. Evidence of pomegranate methanolic extract in antagonizing the endogenous SERM, 27-hydroxycholesterol. IUBMB Life. 2016 Feb;68(2):116-21. doi: 10.1002/iub.1465. Epub 2016 Jan 12. PubMed PMID: 26756990.

7: Raza S, Meyer M, Schommer J, Hammer KD, Guo B, Ghribi O. 27-Hydroxycholesterol stimulates cell proliferation and resistance to docetaxel-induced apoptosis in prostate epithelial cells. Med Oncol. 2016 Feb;33(2):12. doi: 10.1007/s12032-015-0725-5. Epub 2016 Jan 5. PubMed PMID: 26732475.

8: Vurusaner B, Gamba P, Gargiulo S, Testa G, Staurenghi E, Leonarduzzi G, Poli G, Basaga H. Nrf2 antioxidant defense is involved in survival signaling elicited by 27-hydroxycholesterol in human promonocytic cells. Free Radic Biol Med. 2016 Feb;91:93-104. doi: 10.1016/j.freeradbiomed.2015.12.007. Epub 2015 Dec 10. PubMed PMID: 26689473.

9: Marengo B, Bellora F, Ricciarelli R, De Ciucis C, Furfaro A, Leardi R, Colla R, Pacini D, Traverso N, Moretta A, Pronzato MA, Bottino C, Domenicotti C. Oxysterol mixture and, in particular, 27-hydroxycholesterol drive M2 polarization of human macrophages. Biofactors. 2016 Jan-Feb;42(1):80-92. doi: 10.1002/biof.1243. Epub 2015 Dec 16. PubMed PMID: 26669587.

10: Nelson ER. Detection of Endogenous Selective Estrogen Receptor Modulators such as 27-Hydroxycholesterol. Methods Mol Biol. 2016;1366:431-43. doi: 10.1007/978-1-4939-3127-9_34. PubMed PMID: 26585155.

11: Raza S, Ohm JE, Dhasarathy A, Schommer J, Roche C, Hammer KD, Ghribi O. The cholesterol metabolite 27-hydroxycholesterol regulates p53 activity and increases cell proliferation via MDM2 in breast cancer cells. Mol Cell Biochem. 2015 Dec;410(1-2):187-95. doi: 10.1007/s11010-015-2551-7. Epub 2015 Sep 8. PubMed PMID: 26350565; PubMed Central PMCID: PMC4821067.

12: Zhang DD, Yu HL, Ma WW, Liu QR, Han J, Wang H, Xiao R. 27-Hydroxycholesterol contributes to disruptive effects on learning and memory by modulating cholesterol metabolism in the rat brain. Neuroscience. 2015 Aug 6;300:163-73. doi: 10.1016/j.neuroscience.2015.05.022. Epub 2015 May 16. PubMed PMID: 25987203.

13: Gargiulo S, Gamba P, Testa G, Rossin D, Biasi F, Poli G, Leonarduzzi G. Relation between TLR4/NF-κB signaling pathway activation by 27-hydroxycholesterol and 4-hydroxynonenal, and atherosclerotic plaque instability. Aging Cell. 2015 Aug;14(4):569-81. doi: 10.1111/acel.12322. Epub 2015 Mar 10. PubMed PMID: 25757594; PubMed Central PMCID: PMC4531071.

14: Lee WR, Ishikawa T, Umetani M. The interaction between metabolism, cancer and cardiovascular disease, connected by 27-hydroxycholesterol. Clin Lipidol. 2014;9(6):617-624. PubMed PMID: 25632306; PubMed Central PMCID: PMC4306277.

15: Ma WW, Li CQ, Yu HL, Zhang DD, Xi YD, Han J, Liu QR, Xiao R. The oxysterol 27-hydroxycholesterol increases oxidative stress and regulate Nrf2 signaling pathway in astrocyte cells. Neurochem Res. 2015 Apr;40(4):758-66. doi: 10.1007/s11064-015-1524-2. Epub 2015 Jan 29. PubMed PMID: 25630716.

16: Heo W, Kim SM, Eo SK, Rhim BY, Kim K. FSL-1, a Toll-like Receptor 2/6 Agonist, Induces Expression of Interleukin-1α in the Presence of 27-hydroxycholesterol. Korean J Physiol Pharmacol. 2014 Dec;18(6):475-80. doi: 10.4196/kjpp.2014.18.6.475. Epub 2014 Dec 30. PubMed PMID: 25598661; PubMed Central PMCID: PMC4296036.

17: Bandaru VV, Haughey NJ. Quantitative detection of free 24S-hydroxycholesterol, and 27-hydroxycholesterol from human serum. BMC Neurosci. 2014 Dec 24;15:137. doi: 10.1186/s12868-014-0137-z. PubMed PMID: 25539717; PubMed Central PMCID: PMC4304132.

18: Civra A, Cagno V, Donalisio M, Biasi F, Leonarduzzi G, Poli G, Lembo D. Inhibition of pathogenic non-enveloped viruses by 25-hydroxycholesterol and 27-hydroxycholesterol. Sci Rep. 2014 Dec 15;4:7487. doi: 10.1038/srep07487. PubMed PMID: 25501851; PubMed Central PMCID: PMC4265783.

19: Kim SM, Kim BY, Eo SK, Kim CD, Kim K. 27-Hydroxycholesterol up-regulates CD14 and predisposes monocytic cells to superproduction of CCL2 in response to lipopolysaccharide. Biochim Biophys Acta. 2015 Mar;1852(3):442-50. doi: 10.1016/j.bbadis.2014.12.003. Epub 2014 Dec 9. PubMed PMID: 25497142.

20: Heverin M, Maioli S, Pham T, Mateos L, Camporesi E, Ali Z, Winblad B, Cedazo-Minguez A, Björkhem I. 27-hydroxycholesterol mediates negative effects of dietary cholesterol on cognition in mice. Behav Brain Res. 2015 Feb 1;278:356-9. doi: 10.1016/j.bbr.2014.10.018. Epub 2014 Oct 18. PubMed PMID: 25453744.