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

MedKoo CAT#: 527779

CAS#: 64907-22-8

Description: 7alpha,25-OHC is the most potent endogenous EBI2 agonist.

Chemical Structure

CAS# 64907-22-8

Theoretical Analysis

MedKoo Cat#: 527779
Name: 7alpha,25-OHC
CAS#: 64907-22-8
Chemical Formula: C27H46O3
Exact Mass: 418.3447
Molecular Weight: 418.662
Elemental Analysis: C, 77.46; H, 11.08; O, 11.46

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

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Synonym: 7alpha,25-OHC

IUPAC/Chemical Name: 7α,25-Dihydroxyxcholesterol


InChi Code: InChI=1S/C27H46O3/c1-17(7-6-12-25(2,3)30)20-8-9-21-24-22(11-14-27(20,21)5)26(4)13-10-19(28)15-18(26)16-23(24)29/h16-17,19-24,28-30H,6-15H2,1-5H3/t17-,19+,20-,21+,22+,23-,24+,26+,27-/m1/s1

SMILES Code: CC(C)(O)CCC[C@@H](C)[C@H]1CC[C@@]2([H])[C@]3([H])[C@H](O)C=C4C[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: >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).

HS Tariff Code: 2934.99.9001

Preparing Stock Solutions

The following data is based on the product molecular weight 418.662 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.

Recalculate based on batch purity %
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

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4: Vigne S, Chalmin F, Duc D, Clottu AS, Apetoh L, Lobaccaro JA, Christen I, Zhang J, Pot C. IL-27-Induced Type 1 Regulatory T-Cells Produce Oxysterols that Constrain IL-10 Production. Front Immunol. 2017 Sep 25;8:1184. doi: 10.3389/fimmu.2017.01184. eCollection 2017. PubMed PMID: 28993775; PubMed Central PMCID: PMC5622150.

5: Daugvilaite V, Madsen CM, Lückmann M, Echeverria CC, Sailer AW, Frimurer TM, Rosenkilde MM, Benned-Jensen T. Biased agonism and allosteric modulation of G protein-coupled receptor 183 - a 7TM receptor also known as Epstein-Barr virus-induced gene 2. Br J Pharmacol. 2017 Jul;174(13):2031-2042. doi: 10.1111/bph.13801. Epub 2017 May 4. PubMed PMID: 28369721; PubMed Central PMCID: PMC5466542.

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7: Clottu AS, Mathias A, Sailer AW, Schluep M, Seebach JD, Du Pasquier R, Pot C. EBI2 Expression and Function: Robust in Memory Lymphocytes and Increased by Natalizumab in Multiple Sclerosis. Cell Rep. 2017 Jan 3;18(1):213-224. doi: 10.1016/j.celrep.2016.12.006. PubMed PMID: 28052250.

8: Nevius E, Pinho F, Dhodapkar M, Jin H, Nadrah K, Horowitz MC, Kikuta J, Ishii M, Pereira JP. Oxysterols and EBI2 promote osteoclast precursor migration to bone surfaces and regulate bone mass homeostasis. J Exp Med. 2015 Oct 19;212(11):1931-46. doi: 10.1084/jem.20150088. Epub 2015 Oct 5. PubMed PMID: 26438360; PubMed Central PMCID: PMC4612084.

9: Zhang P, He Q, Chen D, Liu W, Wang L, Zhang C, Ma D, Li W, Liu B, Liu F. G protein-coupled receptor 183 facilitates endothelial-to-hematopoietic transition via Notch1 inhibition. Cell Res. 2015 Oct;25(10):1093-107. doi: 10.1038/cr.2015.109. Epub 2015 Sep 11. PubMed PMID: 26358189; PubMed Central PMCID: PMC4650626.

10: Sun S, Liu C. 7α, 25-dihydroxycholesterol-mediated activation of EBI2 in immune regulation and diseases. Front Pharmacol. 2015 Mar 24;6:60. doi: 10.3389/fphar.2015.00060. eCollection 2015. Review. PubMed PMID: 25852561; PubMed Central PMCID: PMC4371701.

11: Chalmin F, Rochemont V, Lippens C, Clottu A, Sailer AW, Merkler D, Hugues S, Pot C. Oxysterols regulate encephalitogenic CD4(+) T cell trafficking during central nervous system autoimmunity. J Autoimmun. 2015 Jan;56:45-55. doi: 10.1016/j.jaut.2014.10.001. Epub 2014 Nov 10. PubMed PMID: 25456971.

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13: Preuss I, Ludwig MG, Baumgarten B, Bassilana F, Gessier F, Seuwen K, Sailer AW. Transcriptional regulation and functional characterization of the oxysterol/EBI2 system in primary human macrophages. Biochem Biophys Res Commun. 2014 Apr 11;446(3):663-8. doi: 10.1016/j.bbrc.2014.01.069. Epub 2014 Jan 27. PubMed PMID: 24480442.

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17: Yi T, Wang X, Kelly LM, An J, Xu Y, Sailer AW, Gustafsson JA, Russell DW, Cyster JG. Oxysterol gradient generation by lymphoid stromal cells guides activated B cell movement during humoral responses. Immunity. 2012 Sep 21;37(3):535-48. doi: 10.1016/j.immuni.2012.06.015. PubMed PMID: 22999953; PubMed Central PMCID: PMC3465460.

18: Zhang L, Shih AY, Yang XV, Kuei C, Wu J, Deng X, Mani NS, Mirzadegan T, Sun S, Lovenberg TW, Liu C. Identification of structural motifs critical for epstein-barr virus-induced molecule 2 function and homology modeling of the ligand docking site. Mol Pharmacol. 2012 Dec;82(6):1094-103. doi: 10.1124/mol.112.080275. Epub 2012 Aug 28. PubMed PMID: 22930711.

19: Benned-Jensen T, Norn C, Laurent S, Madsen CM, Larsen HM, Arfelt KN, Wolf RM, Frimurer T, Sailer AW, Rosenkilde MM. Molecular characterization of oxysterol binding to the Epstein-Barr virus-induced gene 2 (GPR183). J Biol Chem. 2012 Oct 12;287(42):35470-83. doi: 10.1074/jbc.M112.387894. Epub 2012 Aug 8. PubMed PMID: 22875855; PubMed Central PMCID: PMC3471686.

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