MedKoo Cat#: 463752 | Name: Girinimbine

Description:

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

Girinimbine is a natural anti-angiogenic and anti-tumor agent.

Chemical Structure

Girinimbine
Girinimbine
CAS#23095-44-5

Theoretical Analysis

MedKoo Cat#: 463752

Name: Girinimbine

CAS#: 23095-44-5

Chemical Formula: C18H17NO

Exact Mass: 263.1310

Molecular Weight: 263.34

Elemental Analysis: C, 82.10; H, 6.51; N, 5.32; O, 6.08

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 #
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Synonym
Girinimbine; Girinimbin;
IUPAC/Chemical Name
3,3,5-trimethyl-3,11-dihydropyrano[3,2-a]carbazole
InChi Key
GAEQWKVGMHUUKO-UHFFFAOYSA-N
InChi Code
InChI=1S/C18H17NO/c1-11-10-14-12-6-4-5-7-15(12)19-16(14)13-8-9-18(2,3)20-17(11)13/h4-10,19H,1-3H3
SMILES Code
CC1=CC2=C(C3=C1OC(C)(C)C=C3)NC4=C2C=CC=C4
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
>2 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 263.34 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: Liu K, Zang Y, Shen C, Li C, Ma J, Yang J, Sun X, Chen X, Wang N, Zhang D. Synthesis and biological evaluation of pyranocarbazole derivatives as Anti-tumor agents. Bioorg Med Chem Lett. 2020 Dec 13;33:127739. doi: 10.1016/j.bmcl.2020.127739. Epub ahead of print. PMID: 33316408. 2: Mohan S, Hobani YH, Shaheen E, Abou-Elhamd AS, Abdelhaleem A, Alhazmi HA, Abdelwahab SI. Girinimbine from curry leaves promotes gastro protection against ethanol induced peptic ulcers and improves healing via regulation of anti- inflammatory and antioxidant mechanisms. Food Funct. 2020 Apr 30;11(4):3493-3505. doi: 10.1039/d0fo00053a. PMID: 32248216. 3: Hu S, Guo JM, Zhang WH, Zhang MM, Liu YP, Fu YH. [Chemical constituents from stems and leaves of Clausena emarginata]. Zhongguo Zhong Yao Za Zhi. 2019 May;44(10):2096-2101. Chinese. doi: 10.19540/j.cnki.cjcmm.20190321.204. PMID: 31355567. 4: Maruthanila VL, Elancheran R, Kunnumakkar AB, Kabilan S, Kotoky J. Pleiotropic Effect of Mahanine and Girinimbine Analogs: Anticancer Mechanism and its Therapeutic Versatility. Anticancer Agents Med Chem. 2018;18(14):1983-1990. doi: 10.2174/1871520618666180830151720. PMID: 30173653. 5: Xin Q, Muer A. Girinimbine Inhibits the Proliferation of Human Ovarian Cancer Cells In Vitro via the Phosphatidylinositol-3-Kinase (PI3K)/Akt and the Mammalian Target of Rapamycin (mTOR) and Wnt/β-Catenin Signaling Pathways. Med Sci Monit. 2018 Aug 7;24:5480-5487. doi: 10.12659/MSM.910137. PMID: 30084434; PMCID: PMC6094984. 6: Iman V, Mohan S, Abdelwahab SI, Karimian H, Nordin N, Fadaeinasab M, Noordin MI, Noor SM. Anticancer and anti-inflammatory activities of girinimbine isolated from Murraya koenigii. Drug Des Devel Ther. 2016 Dec 28;11:103-121. doi: 10.2147/DDDT.S115135. PMID: 28096658; PMCID: PMC5207336. 7: Nalli Y, Khajuria V, Gupta S, Arora P, Riyaz-Ul-Hassan S, Ahmed Z, Ali A. Four new carbazole alkaloids from Murraya koenigii that display anti- inflammatory and anti-microbial activities. Org Biomol Chem. 2016 Mar 28;14(12):3322-32. doi: 10.1039/c6ob00267f. Erratum in: Org Biomol Chem. 2018 Mar 14;16(11):1994. PMID: 26947457. 8: Iman V, Karimian H, Mohan S, Hobani YH, Noordin MI, Mustafa MR, Noor SM. In vitro and in vivo anti-angiogenic activity of girinimbine isolated from Murraya koenigii. Drug Des Devel Ther. 2015 Mar 3;9:1281-92. doi: 10.2147/DDDT.S71557. PMID: 25767375; PMCID: PMC4354401. 9: Hesse R, Gruner KK, Kataeva O, Schmidt AW, Knölker HJ. Efficient construction of pyrano[3,2-a]carbazoles: application to a biomimetic total synthesis of cyclized monoterpenoid pyrano[3,2-a]carbazole alkaloids. Chemistry. 2013 Oct 11;19(42):14098-111. doi: 10.1002/chem.201301792. Epub 2013 Sep 12. PMID: 24030919. 10: Mohan S, Abdelwahab SI, Cheah SC, Sukari MA, Syam S, Shamsuddin N, Rais Mustafa M. Apoptosis Effect of Girinimbine Isolated from Murraya koenigii on Lung Cancer Cells In Vitro. Evid Based Complement Alternat Med. 2013;2013:689865. doi: 10.1155/2013/689865. Epub 2013 Mar 13. PMID: 23573145; PMCID: PMC3610346. 11: Songue JL, Kouam, Dongo E, Mpondo TN, White RL. Chemical constituents from stem bark and roots of Clausena anisata. Molecules. 2012 Nov 20;17(11):13673-86. doi: 10.3390/molecules171113673. PMID: 23169265; PMCID: PMC6268541. 12: Kok YY, Mooi LY, Ahmad K, Sukari MA, Mat N, Rahmani M, Ali AM. Anti-tumour promoting activity and antioxidant properties of girinimbine isolated from the stem bark of Murraya koenigii S. Molecules. 2012 Apr 20;17(4):4651-60. doi: 10.3390/molecules17044651. PMID: 22522395; PMCID: PMC6268782. 13: Sim KM, Teh HM. A new carbazole alkaloid from the leaves of Malayan Murraya koenigii. J Asian Nat Prod Res. 2011 Oct;13(10):972-5. doi: 10.1080/10286020.2011.602970. PMID: 21972815. 14: Syam S, Abdul AB, Sukari MA, Mohan S, Abdelwahab SI, Wah TS. The growth suppressing effects of girinimbine on HepG2 involve induction of apoptosis and cell cycle arrest. Molecules. 2011 Aug 23;16(8):7155-70. doi: 10.3390/molecules16087155. PMID: 21862957; PMCID: PMC6264672. 15: Gruner KK, Hopfmann T, Matsumoto K, Jäger A, Katsuki T, Knölker HJ. Efficient iron-mediated approach to pyrano[3,2-a]carbazole alkaloids--first total syntheses of O-methylmurrayamine A and 7-methoxymurrayacine, first asymmetric synthesis and assignment of the absolute configuration of (-)-trans- dihydroxygirinimbine. Org Biomol Chem. 2011 Apr 7;9(7):2057-61. doi: 10.1039/c0ob01088j. Epub 2011 Jan 31. PMID: 21279228. 16: Chakraborty M, Saha S, Mukhapadhyay S. Murrayakoeninol--a new carbazole alkaloid from Murraya koenigii (Linn) Spreng. Nat Prod Commun. 2009 Mar;4(3):355-8. PMID: 19413112. 17: Adebajo AC, Ayoola OF, Iwalewa EO, Akindahunsi AA, Omisore NO, Adewunmi CO, Adenowo TK. Anti-trichomonal, biochemical and toxicological activities of methanolic extract and some carbazole alkaloids isolated from the leaves of Murraya koenigii growing in Nigeria. Phytomedicine. 2006 Mar;13(4):246-54. doi: 10.1016/j.phymed.2004.12.002. Epub 2005 Sep 19. PMID: 16492527. 18: Zou L, Yang C, Zhang H. [Study on carbazole alkaloids of Murraya microphylla]. Zhong Yao Cai. 1999 Sep;22(9):458-60. Chinese. PMID: 12571921. 19: Cui CB, Yan SY, Cai B, Yao XS. Carbazole alkaloids as new cell cycle inhibitor and apoptosis inducers from Clausena dunniana Levl. J Asian Nat Prod Res. 2002 Dec;4(4):233-41. doi: 10.1080/1028602021000049041. PMID: 12450250. 20: Ko FN, Lee YS, Wu TS, Teng CM. Inhibition of cyclooxygenase activity and increase in platelet cyclic AMP by girinimbine, isolated from Murraya euchrestifolia. Biochem Pharmacol. 1994 Jul 19;48(2):353-60. doi: 10.1016/0006-2952(94)90107-4. PMID: 8053931.