phytomedicinal | predominant naphthodianthrone | CAS#55954-61-5 | kinase C | dopamine-β-hydroxylase

MedKoo Cat#: 126019 | Name: Pseudohypericin

Description:

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

Pseudohypericin is a predominant naphthodianthrone from St. John’s wort (Hypericum perforatum L.) phytomedicinal drug. It has been shown to specifically inhibit protein kinase C and dopamine-β-hydroxylase. Also, pseudohypericin induces apoptosis and selectively antagonizes corticotropin-releasing factor in murine models.

Chemical Structure

Pseudohypericin

CAS#55954-61-5

Theoretical Analysis

MedKoo Cat#: 126019

Name: Pseudohypericin

CAS#: 55954-61-5

Chemical Formula: C30H16O9

Exact Mass: 520.0794

Molecular Weight: 520.45

Elemental Analysis: C, 69.23; H, 3.10; O, 27.67

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.

Bulk Inquiry

Related CAS #

No Data

Synonym

Pseudohypericin; HSDB 8107; NSC624609; NSC-624609

IUPAC/Chemical Name

1,3,4,6,8,13-hexahydroxy-10-(hydroxymethyl)-11-methylphenanthro[1,10,9,8-opqra]perylene-7,14-dione

InChi Key

YXBUQQDFTYOHQI-UHFFFAOYSA-N

InChi Code

InChI=1S/C30H16O9/c1-7-2-9(32)19-23-15(7)16-8(6-31)3-10(33)20-24(16)28-26-18(12(35)5-14(37)22(26)30(20)39)17-11(34)4-13(36)21(29(19)38)25(17)27(23)28/h2-5,31-37H,6H2,1H3

SMILES Code

CC1=C2C3=C(CO)C=C(O)C4=C3C5=C6C2=C(C(O)=C1)C(=O)C7=C6C(=C(O)C=C7O)C8=C(O)C=C(O)C(C4=O)=C58

Appearance

To be determined

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

To be determined

Shelf Life

>2 years if stored properly

Drug Formulation

To be determined

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

More Info

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 520.45 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

1: Vandenbogaerde AL, Kamuhabwa A, Delaey E, Himpens BE, Merlevede WJ, de Witte PA. Photocytotoxic effect of pseudohypericin versus hypericin. J Photochem Photobiol B. 1998 Sep;45(2-3):87-94. doi: 10.1016/s1011-1344(98)00163-8. PMID: 9868799. 2: Kitanov GM. Hypericin and pseudohypericin in some Hypericum species. Biochem Syst Ecol. 2001 Feb 1;29(2):171-178. doi: 10.1016/s0305-1978(00)00032-6. PMID: 11106845. 3: Staffeldt B, Kerb R, Brockmöller J, Ploch M, Roots I. Pharmacokinetics of hypericin and pseudohypericin after oral intake of the hypericum perforatum extract LI 160 in healthy volunteers. J Geriatr Psychiatry Neurol. 1994 Oct;7 Suppl 1:S47-53. doi: 10.1177/089198879400700113. PMID: 7857509. 4: Brockmöller J, Reum T, Bauer S, Kerb R, Hübner WD, Roots I. Hypericin and pseudohypericin: pharmacokinetics and effects on photosensitivity in humans. Pharmacopsychiatry. 1997 Sep;30 Suppl 2:94-101. doi: 10.1055/s-2007-979527. PMID: 9342768. 5: Gadzovska S, Maury S, Ounnar S, Righezza M, Kascakova S, Refregiers M, Spasenoski M, Joseph C, Hagège D. Identification and quantification of hypericin and pseudohypericin in different Hypericum perforatum L. in vitro cultures. Plant Physiol Biochem. 2005 Jun;43(6):591-601. doi: 10.1016/j.plaphy.2005.05.005. PMID: 15979315. 6: Takahashi I, Nakanishi S, Kobayashi E, Nakano H, Suzuki K, Tamaoki T. Hypericin and pseudohypericin specifically inhibit protein kinase C: possible relation to their antiretroviral activity. Biochem Biophys Res Commun. 1989 Dec 29;165(3):1207-12. doi: 10.1016/0006-291x(89)92730-7. PMID: 2558652. 7: Ciogli A, Bicker W, Lindner W. Determination of enantiomerization barriers of hypericin and pseudohypericin by dynamic high-performance liquid chromatography on immobilized polysaccharide-type chiral stationary phases and off-column racemization experiments. Chirality. 2010 May 15;22(5):463-71. doi: 10.1002/chir.20764. PMID: 19644936. 8: Chen XG, Hua F, Wang SG, Xu YY, Yue HT, Sun J. Zafirlukast in combination with pseudohypericin attenuates spinal cord injury and motor function in experimental mice. Drug Des Devel Ther. 2018 Aug 1;12:2389-2402. doi: 10.2147/DDDT.S154814. Erratum in: Drug Des Devel Ther. 2021 Feb 09;15:419-422. PMID: 30122897; PMCID: PMC6078184. 9: Lavie G, Valentine F, Levin B, Mazur Y, Gallo G, Lavie D, Weiner D, Meruelo D. Studies of the mechanisms of action of the antiretroviral agents hypericin and pseudohypericin. Proc Natl Acad Sci U S A. 1989 Aug;86(15):5963-7. doi: 10.1073/pnas.86.15.5963. PMID: 2548193; PMCID: PMC297751. 10: Xenophontos M, Stavropoulos E, Avramakis E, Navakoudis E, Dörnemann D, Kotzabasis K. Influence of the developmental stage on the (proto)-hypericin and (proto)pseudohypericin levels of Hypericum plants from Crete. Planta Med. 2007 Oct;73(12):1309-15. doi: 10.1055/s-2007-990222. Epub 2007 Sep 24. PMID: 17893828.