20(S)-Hydroxycholesterol

Synonyms	20-hydroxycholesterol; 20alpha-Hydroxycholesterol; (20S)-20-Hydroxycholesterol; cholest-5-en-3beta,20-diol; 20S-Cholest-5-ene-3beta,20-diol; 20α-hydroxycholesterol
IUPACName	(3S,8S,9S,10R,13S,14S,17S)-17-[(2S)-2-hydroxy-6-methylheptan-2-yl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol
CanonicalSMILES	CC(C)CCCC(C)(C1CCC2C1(CCC3C2CC=C4C3(CCC(C4)O)C)C)O
InChI	InChI=1S/C27H46O2/c1-18(2)7-6-14-27(5,29)24-11-10-22-21-9-8-19-17-20(28)12-15-25(19,3)23(21)13-16-26(22,24)4/h8,18,20-24,28-29H,6-7,9-17H2,1-5H3/t20-,21-,22-,23-,24-,25-,26-,27-/m0/s1
InChIKey	MCKLJFJEQRYRQT-APGJSSKUSA-N
MeltingPoint	125-132°C
Purity	>99%
Solubility	Soluble in Chloroform and Methanol
ShelfLife	3 months
ExactMass	402.35
Hygroscopic	No
LightSensitive	No
PercentComposition	C 80.54%, H 11.51%, O 7.95%

20(S)-Hydroxycholesterol, a significant oxysterol, has garnered attention in various scientific fields for its crucial roles in cell biology and medicine. One of its key applications lies in cholesterol metabolism regulation. As an oxysterol, 20(S)-Hydroxycholesterol is involved in the homeostasis of cholesterol by acting as a ligand for liver X receptors (LXRs). LXRs are nuclear receptors that regulate the expression of genes necessary for cholesterol efflux, transport, and excretion. By modulating these pathways, 20(S)-Hydroxycholesterol helps maintain cholesterol balance in cells, which is vital for preventing lipid disorders and related diseases such as atherosclerosis.

Another essential application of 20(S)-Hydroxycholesterol is in the differentiation of stem cells. Specifically, 20(S)-Hydroxycholesterol has been shown to influence the differentiation of mesenchymal stem cells into osteoblasts—cells responsible for bone formation. This functionality is attributed to its ability to activate the Hedgehog signaling pathway, which plays a pivotal role in the development and regeneration of bone tissue. Consequently, 20(S)-Hydroxycholesterol holds promise as a potential therapeutic agent in treating bone-related disorders such as osteoporosis and enhancing bone regeneration in orthopedic surgeries.

Moreover, 20(S)-Hydroxycholesterol exhibits significant immunomodulatory properties, making it a valuable compound in the field of immunotherapy. It interacts with various immune cells, including macrophages and dendritic cells, and influences their function and activity. For example, it has been reported to affect the production of pro-inflammatory cytokines and enhance the phagocytic activity of macrophages. These properties suggest that 20(S)-Hydroxycholesterol could be utilized to modulate immune responses in autoimmune diseases, infections, and cancer, offering a targeted approach to enhance the efficacy of existing immunotherapies.

Lastly, 20(S)-Hydroxycholesterol shows potential in neurobiology research and therapeutic applications. It has been implicated in the development and maintenance of the central nervous system (CNS). The oxysterol participates in myelination processes by influencing the differentiation of oligodendrocyte precursor cells into mature oligodendrocytes, which are essential for the formation of myelin sheaths around nerve fibers. Myelin is crucial for the proper conduction of electrical signals in the CNS. Therefore, 20(S)-Hydroxycholesterol could be explored as a candidate for addressing demyelinating conditions such as multiple sclerosis, aiming to promote remyelination and restore neural function.

1. Abrams ME, Johnson KA, Perelman SS, Zhang LS, Endapally S, Mar KB, Thompson BM, McDonald JG, Schoggins JW, Radhakrishnan A, Alto NM. Oxysterols provide innate immunity to bacterial infection by mobilizing cell surface accessible cholesterol. Nat Microbiol. 2020 Apr 13. doi: 10.1038/s41564-020-0701-5. Epub ahead of print. PMID: 32284563. PubMed ID: 32284563.
2. Zhang Z, Yomo D, Gradinaru C. Choosing the right fluorophore for single-molecule fluorescence studies in a lipid environment. Biochim Biophys Acta Biomembr. 2017 Jul;1859(7):1242-1253. doi: 10.1016/j.bbamem.2017.04.001. Epub 2017 Apr 6. PMID: 28392350. PubMed ID: 28392350.