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MedKoo Cat#: 584845 | Name: Cassaine

Description:

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

Cassaine is an erythrophleum alkaloid.

Chemical Structure

Cassaine
Cassaine
CAS#468-76-8

Theoretical Analysis

MedKoo Cat#: 584845

Name: Cassaine

CAS#: 468-76-8

Chemical Formula: C24H39NO4

Exact Mass: 405.2879

Molecular Weight: 405.58

Elemental Analysis: C, 71.07; H, 9.69; N, 3.45; O, 15.78

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.
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Related CAS #
No Data
Synonym
Cassaine; Nervocidine
IUPAC/Chemical Name
Acetic acid, (dodecahydro-7-hydroxy-1,4b,8,8-tetramethyl-10-oxo-2(1H)-phenanthrenylidene)-, 2-(dimethylamino)ethyl ester, (1R-(1alpha,2E,4aalpha,4bbeta,7beta,8aalpha,10abeta))-
InChi Key
GMHWATCMBXIANN-IOJUAHGHSA-N
InChi Code
InChI=1S/C24H39NO4/c1-15-16(13-21(28)29-12-11-25(5)6)7-8-17-22(15)18(26)14-19-23(2,3)20(27)9-10-24(17,19)4/h13,15,17,19-20,22,27H,7-12,14H2,1-6H3/b16-13+/t15-,17-,19-,20-,22-,24+/m0/s1
SMILES Code
O=C(OCCN(C)C)/C=C(CC[C@]1([H])[C@@]2(C)CC[C@H](O)C(C)(C)[C@]2([H])C3)/[C@H](C)[C@]1([H])C3=O
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

Preparing Stock Solutions

The following data is based on the product molecular weight 405.58 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
1: Ha MT, Tran MH, Phuong TT, Kim JA, Woo MH, Choi JS, Lee S, Lee JH, Lee HK, Min BS. Cytotoxic and apoptosis-inducing activities against human lung cancer cell lines of cassaine diterpenoids from the bark of Erythrophleum fordii. Bioorg Med Chem Lett. 2017 Jul 1;27(13):2946-2952. doi: 10.1016/j.bmcl.2017.05.006. Epub 2017 May 4. PubMed PMID: 28506750. 2: Hung TM, Cuong TD, Kim JA, Tae N, Lee JH, Min BS. Cassaine diterpene alkaloids from Erythrophleum fordii and their anti-angiogenic effect. Bioorg Med Chem Lett. 2014 Jan 1;24(1):168-72. doi: 10.1016/j.bmcl.2013.11.048. Epub 2013 Nov 27. PubMed PMID: 24332631. 3: Ravindar K, Caron PY, Deslongchamps P. Anionic polycyclization entry to tricycles related to quassinoids and terpenoids: a stereocontrolled total synthesis of (+)-cassaine. J Org Chem. 2014 Sep 5;79(17):7979-99. doi: 10.1021/jo501122k. Epub 2014 Aug 7. PubMed PMID: 25057897. 4: Hung TM, Cuong TD, Kim JA, Lee JH, Woo MH, Min BS. In vitro apoptotic effect of cassaine-type diterpene amides from Erythrophleum fordii on PC-3 prostate cancer cells. Bioorg Med Chem Lett. 2014 Nov 1;24(21):4989-94. doi: 10.1016/j.bmcl.2014.09.025. Epub 2014 Sep 16. PubMed PMID: 25278231. 5: Du D, Qu J, Wang JM, Yu SS, Chen XG, Xu S, Ma SG, Li Y, Ding GZ, Fang L. Cytotoxic cassaine diterpenoid-diterpenoid amide dimers and diterpenoid amides from the leaves of Erythrophleum fordii. Phytochemistry. 2010 Oct;71(14-15):1749-55. doi: 10.1016/j.phytochem.2010.07.004. Epub 2010 Aug 2. PubMed PMID: 20678783. 6: Tae N, Hung TM, Kim O, Kim N, Lee S, Na S, Min BS, Lee JH. A cassaine diterpene alkaloid, 3β-acetyl-nor-erythrophlamide, suppresses VEGF-induced angiogenesis and tumor growth via inhibiting eNOS activation. Oncotarget. 2017 Sep 28;8(54):92346-92358. doi: 10.18632/oncotarget.21307. eCollection 2017 Nov 3. PubMed PMID: 29190920; PubMed Central PMCID: PMC5696186. 7: COTTEN MD, GOLDBERG LI, WALTON RP. Cassaine and cassaidine: quantitative measurements of heart contractile force in situ. J Pharmacol Exp Ther. 1952 Sep;106(1):94-102. PubMed PMID: 14955792. 8: Ravindar K, Caron PY, Deslongchamps P. Total synthesis of (+)-cassaine utilizing an anionic polycyclization strategy. Org Lett. 2013 Dec 20;15(24):6270-3. doi: 10.1021/ol4030937. Epub 2013 Dec 2. PubMed PMID: 24295200. 9: Ngo TC, Nguyen TH, Dao DQ. Radical Scavenging Activity of Natural-Based Cassaine Diterpenoid Amides and Amines. J Chem Inf Model. 2019 Feb 25;59(2):766-776. doi: 10.1021/acs.jcim.8b00847. Epub 2019 Feb 6. PubMed PMID: 30681326. 10: Armah FA, Amponsah IK, Mensah AY, Dickson RA, Steenkamp PA, Madala NE, Adokoh CK. Leishmanicidal activity of the root bark of Erythrophleum Ivorense (Fabaceae) and identification of some of its compounds by ultra-performance liquid chromatography quadrupole time of flight mass spectrometry (UPLC-QTOF-MS/MS). J Ethnopharmacol. 2018 Jan 30;211:207-216. doi: 10.1016/j.jep.2017.09.030. Epub 2017 Sep 29. PubMed PMID: 28970156. 11: Tobin T, Akera T, Brody TM, Taneja HR. Studies on the stable inhibition of Na+ + K+-ATPase by cassaine. Eur J Pharmacol. 1976 Jan;35(1):59-68. PubMed PMID: 130244. 12: Huang X, Chen Z, Zhou S, Huang P, Zhuo Z, Zeng S, Wang L, Wang Y, Xu C, Tian H. Cassaine diterpenoids from the seeds of Erythrophleum fordii and their cytotoxic activities. Fitoterapia. 2018 Jun;127:245-251. doi: 10.1016/j.fitote.2018.02.028. Epub 2018 Feb 26. PubMed PMID: 29496564. 13: Tobin T, Akera T, Brody SL, Ku D, Brody TM. Cassaine: mechanism of inhibition of Na+ +K+ -ATPase and relationship of this inhibition to cardiotonic actions. Eur J Pharmacol. 1975 Jun-Jul;32(02):133-45. PubMed PMID: 125204. 14: Du D, Fang L, Qu J, Yu S, Ma S, Lv H, Liu J, Liu Y, Wang J, Wang X. Oleanane-type triterpene saponins and cassaine-type diterpenoids from Erythrophleum fordii. Planta Med. 2011 Sep;77(14):1631-8. doi: 10.1055/s-0030-1270992. Epub 2011 Apr 11. PubMed PMID: 21484673. 15: Qu J, Hu YC, Yu SS, Chen XG, Li Y. New cassaine diterpenoid amides with cytotoxic activities from the bark of Erythrophleum fordii. Planta Med. 2006 Apr;72(5):442-9. PubMed PMID: 16557459. 16: Armah FA, Annan K, Mensah AY, Amponsah IK, Tocher DA, Habtemariam S. Erythroivorensin: A novel anti-inflammatory diterpene from the root-bark of Erythrophleum ivorense (A Chev.). Fitoterapia. 2015 Sep;105:37-42. doi: 10.1016/j.fitote.2015.06.001. Epub 2015 Jun 6. PubMed PMID: 26057191. 17: De Munari S, Barassi P, Cerri A, Fedrizzi G, Gobbini M, Mabilia M, Melloni P. A new approach to the design of novel inhibitors of Na+,K+-ATPase: 17alpha-substituted seco-D 5beta-androstane as cassaine analogues. J Med Chem. 1998 Jul 30;41(16):3033-40. PubMed PMID: 9685243. 18: Qu J, Wang YH, Li JB, Yu SS, Li Y, Liu YB. Rapid structural determination of new trace cassaine-type diterpenoid amides in fractions from Erythrophleum fordii by liquid chromatography-diode-array detection/electrospray ionization tandem mass spectrometry and liquid chromatography/nuclear magnetic resonance. Rapid Commun Mass Spectrom. 2007;21(13):2109-19. PubMed PMID: 17551997. 19: KAHN JB Jr, VANATTA RA Jr, JOHNSON GL. SOME EFFECTS OF CASSAINE ON CARDIOVASCULAR DYNAMICS IN THE DOG. J Pharmacol Exp Ther. 1963 Nov;142:215-22. PubMed PMID: 14079658. 20: Clarke RL, Daum SJ, Shaw PE, Brown TG Jr, Groblewski GE, O'Connor WV. Cassaine analogs. IV. Distant analogs of cassaine. J Med Chem. 1967 Jul;10(4):593-7. PubMed PMID: 6037045.

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