Calanolide B | CAS# 142632-33-5 | HIV-inhibiting coumarins

MedKoo Cat#: 412229 | Name: Calanolide B

Description:

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

Calanolide B is one of a novel class of HIV-inhibiting coumarins from the tropical rainforest tree, Calophyllum lanigerum.

Chemical Structure

Calanolide B

CAS#142632-33-5

Theoretical Analysis

MedKoo Cat#: 412229

Name: Calanolide B

CAS#: 142632-33-5

Chemical Formula: C22H26O5

Exact Mass: 370.1800

Molecular Weight: 370.45

Elemental Analysis: C, 71.33; H, 7.07; O, 21.59

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

Calanolide B; CCRIS-9389; CCRIS9389; CCRIS 9389

IUPAC/Chemical Name

2H,6H,10H-Benzo(1,2-b:3,4-b':5,6-b'')tripyran-2-one, 11,12-dihydro-12-hydroxy-6,6,10,11-tetramethyl-4-propyl-, (10R,11S,12R)-

InChi Key

NIDRYBLTWYFCFV-SEDUGSJDSA-N

InChi Code

InChI=1S/C22H26O5/c1-6-7-13-10-15(23)26-21-16(13)20-14(8-9-22(4,5)27-20)19-17(21)18(24)11(2)12(3)25-19/h8-12,18,24H,6-7H2,1-5H3/t11-,12-,18-/m1/s1

SMILES Code

O=C1C=C(CCC)C2=C3C(C=CC(C)(C)O3)=C4C([C@H](O)[C@H](C)[C@@H](C)O4)=C2O1

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

2934.99.9001

More Info

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 370.45 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: César GZ, Alfonso MG, Marius MM, Elizabeth EM, Angel CB, Maira HR, Guadalupe CL, Manuel JE, Ricardo RC. Inhibition of HIV-1 reverse transcriptase, toxicological and chemical profile of Calophyllum brasiliense extracts from Chiapas, Mexico. Fitoterapia. 2011 Oct;82(7):1027-34. doi: 10.1016/j.fitote.2011.06.006. Epub 2011 Jun 24. PMID: 21723379. 2: Xu ZQ, Norris KJ, Weinberg DS, Kardatzke J, Wertz P, Frank P, Flavin MT. Quantification of (+)-calanolide A, a novel and naturally occurring anti-HIV agent, by high-performance liquid chromatography in plasma from rat, dog and human. J Chromatogr B Biomed Sci Appl. 2000 Jun 9;742(2):267-75. doi: 10.1016/s0378-4347(00)00170-5. PMID: 10901131. 3: Buckheit RW Jr, White EL, Fliakas-Boltz V, Russell J, Stup TL, Kinjerski TL, Osterling MC, Weigand A, Bader JP. Unique anti-human immunodeficiency virus activities of the nonnucleoside reverse transcriptase inhibitors calanolide A, costatolide, and dihydrocostatolide. Antimicrob Agents Chemother. 1999 Aug;43(8):1827-34. doi: 10.1128/AAC.43.8.1827. PMID: 10428899; PMCID: PMC89377. 4: Spino C, Dodier M, Sotheeswaran S. Anti-HIV coumarins from Calophyllum seed oil. Bioorg Med Chem Lett. 1998 Dec 15;8(24):3475-8. doi: 10.1016/s0960-894x(98)00628-3. PMID: 9934455. 5: McKee TC, Covington CD, Fuller RW, Bokesch HR, Young S, Cardellina II JH, Kadushin MR, Soejarto DD, Stevens PF, Cragg GM, Boyd MR. Pyranocoumarins from tropical species of the genus Calophyllum: a chemotaxonomic study of extracts in the National Cancer Institute collection. J Nat Prod. 1998 Oct;61(10):1252-6. doi: 10.1021/np980140a. PMID: 9784162. 6: Newman RA, Chen W, Madden TL. Pharmaceutical properties of related calanolide compounds with activity against human immunodeficiency virus. J Pharm Sci. 1998 Sep;87(9):1077-80. doi: 10.1021/js980122d. PMID: 9724557. 7: Galinis DL, Fuller RW, McKee TC, Cardellina JH 2nd, Gulakowski RJ, McMahon JB, Boyd MR. Structure-activity modifications of the HIV-1 inhibitors (+)-calanolide A and (-)-calanolide B. J Med Chem. 1996 Oct 25;39(22):4507-10. doi: 10.1021/jm9602827. PMID: 8893846. 8: Kashman Y, Gustafson KR, Fuller RW, Cardellina JH 2nd, McMahon JB, Currens MJ, Buckheit RW Jr, Hughes SH, Cragg GM, Boyd MR. The calanolides, a novel HIV- inhibitory class of coumarin derivatives from the tropical rainforest tree, Calophyllum lanigerum. J Med Chem. 1992 Jul 24;35(15):2735-43. doi: 10.1021/jm00093a004. Erratum in: J Med Chem 1993 Apr 16;36(8):1110. PMID: 1379639.