Calanolide B

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

MedKoo CAT#: 412229

CAS#: 142632-33-5

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


Chemical Structure

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Calanolide B
CAS# 142632-33-5

Theoretical Analysis

MedKoo Cat#: 412229
Name: Calanolide B
CAS#: 142632-33-5
Chemical Formula: C22H26O5
Exact Mass: 370.18
Molecular Weight: 370.45
Elemental Analysis: C, 71.33; H, 7.07; O, 21.59

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: 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

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.

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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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.