Myricanone

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

MedKoo CAT#: 534867

CAS#: 32492-74-3

Description: Myricanone is from stem bark of Myrica rubra.


Chemical Structure

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Myricanone
CAS# 32492-74-3

Theoretical Analysis

MedKoo Cat#: 534867
Name: Myricanone
CAS#: 32492-74-3
Chemical Formula: C21H24O5
Exact Mass: 356.1624
Molecular Weight: 356.418
Elemental Analysis: C, 70.77; H, 6.79; O, 22.44

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.

Request quote for custom synthesis

Synonym: Myricanone

IUPAC/Chemical Name: Tricyclo(12.3.1.12,6)nonadeca-1(18),2,4,6(19),14,16-hexaen-9-one, 3,15-dihydroxy-16,17-dimethoxy-

InChi Key: ZTSNTUQTNQSIDC-UHFFFAOYSA-N

InChi Code: InChI=1S/C21H24O5/c1-25-20-17-12-14(19(24)21(20)26-2)5-3-4-6-15(22)9-7-13-8-10-18(23)16(17)11-13/h8,10-12,23-24H,3-7,9H2,1-2H3

SMILES Code: O=C(CCCC1)CCC2=CC(C3=CC1=C(O)C(OC)=C3OC)=C(O)C=C2

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 356.418 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: Paul A, Das S, Das J, Samadder A, Bishayee K, Sadhukhan R, Khuda-Bukhsh AR. Diarylheptanoid-myricanone isolated from ethanolic extract of Myrica cerifera shows anticancer effects on HeLa and PC3 cell lines: signalling pathway and drug-DNA interaction. J Integr Med. 2013 Nov;11(6):405-15. doi: 10.3736/jintegrmed2013057. PMID: 24299604.

2: Dai G, Tong Y, Chen X, Ren Z, Yang F. In vitro Anticancer Activity of Myricanone in Human Lung Adenocarcinoma A549 Cells. Chemotherapy. 2014;60(2):81-7. doi: 10.1159/000371738. PMID: 25720464.

3: Paul A, Das J, Das S, Samadder A, Khuda-Bukhsh AR. Anticancer potential of myricanone, a major bioactive component of Myrica cerifera: novel signaling cascade for accomplishing apoptosis. J Acupunct Meridian Stud. 2013 Aug;6(4):188-98. doi: 10.1016/j.jams.2013.05.003. Epub 2013 Jun 15. PMID: 23972241.

4: Makule E, Schmidt TJ, Heilmann J, Kraus B. Diarylheptanoid Glycosides of Morella salicifolia Bark. Molecules. 2017 Dec 19;22(12):2266. doi: 10.3390/molecules22122266. PMID: 29257058; PMCID: PMC6149793.

5: Kabra A, Sharma R, Hano C, Kabra R, Martins N, Baghel US. Phytochemical Composition, Antioxidant, and Antimicrobial Attributes of Different Solvent Extracts from Myrica esculenta Buch.-Ham. ex. D. Don Leaves. Biomolecules. 2019 Aug 9;9(8):357. doi: 10.3390/biom9080357. PMID: 31405047; PMCID: PMC6724038.

6: R M Ibrahim S, A Mohamed G, I M Khedr A, M Aljaeid B. Anti-oxidant and Anti- Inflammatory Cyclic Diarylheptanoids from Alnus japonica Stem Bark. Iran J Pharm Res. 2017 Winter;16(Suppl):83-91. PMID: 29844779; PMCID: PMC5963649.

7: Matsuda H, Yamazaki M, Matsuo K, Asanuma Y, Kubo M. Anti-androgenic activity of Myricae Cortex--isolation of active constituents from bark of Myrica rubra. Biol Pharm Bull. 2001 Mar;24(3):259-63. doi: 10.1248/bpb.24.259. PMID: 11256481.

8: Inoue T. [Constituents of Acer nikoense and Myrica rubra. On diarylheptanoids]. Yakugaku Zasshi. 1993 Mar;113(3):181-97. Japanese. doi: 10.1248/yakushi1947.113.3_181. PMID: 8509989.

9: Yoshimura M, Yamakami S, Amakura Y, Yoshida T. Diarylheptanoid sulfates and related compounds from Myrica rubra bark. J Nat Prod. 2012 Oct 26;75(10):1798-802. doi: 10.1021/np300212c. Epub 2012 Oct 15. PMID: 23066712.

10: Tao J, Morikawa T, Toguchida I, Ando S, Matsuda H, Yoshikawa M. Inhibitors of nitric oxide production from the bark of Myrica rubra: structures of new biphenyl type diarylheptanoid glycosides and taraxerane type triterpene. Bioorg Med Chem. 2002 Dec;10(12):4005-12. doi: 10.1016/s0968-0896(02)00314-0. PMID: 12413852.

11: Ting YC, Ko HH, Wang HC, Peng CF, Chang HS, Hsieh PC, Chen IS. Biological evaluation of secondary metabolites from the roots of Myrica adenophora. Phytochemistry. 2014 Jul;103:89-98. doi: 10.1016/j.phytochem.2014.04.003. Epub 2014 May 5. PMID: 24810013.

12: Ishida J, Kozuka M, Tokuda H, Nishino H, Nagumo S, Lee KH, Nagai M. Chemopreventive potential of cyclic diarylheptanoids. Bioorg Med Chem. 2002 Oct;10(10):3361-5. doi: 10.1016/s0968-0896(02)00164-5. PMID: 12150883.

13: Shen SN, Xia FB, Li H, Liu YM, Pan RL. [A new cyclic diarylheptanoid from the bark of Myrica rubra]. Yao Xue Xue Bao. 2015 Jun;50(6):746-8. Chinese. PMID: 26521447.

14: Liu TH, Chen WH, Chen XD, Liang QE, Tao WC, Jin Z, Xiao Y, Chen LG. Network Pharmacology Identifies the Mechanisms of Action of TaohongSiwu Decoction Against Essential Hypertension. Med Sci Monit. 2020 Mar 18;26:e920682. doi: 10.12659/MSM.920682. PMID: 32187175; PMCID: PMC7102407.

15: Zhang J, Yamada S, Ogihara E, Kurita M, Banno N, Qu W, Feng F, Akihisa T. Biological Activities of Triterpenoids and Phenolic Compounds from Myrica cerifera Bark. Chem Biodivers. 2016 Nov;13(11):1601-1609. doi: 10.1002/cbdv.201600247. Epub 2016 Oct 19. PMID: 27492128.

16: Akazawa H, Fujita Y, Banno N, Watanabe K, Kimura Y, Manosroi A, Manosroi J, Akihisa T. Three new cyclic diarylheptanoids and other phenolic compounds from the bark of Myrica rubra and their melanogenesis inhibitory and radical scavenging activities. J Oleo Sci. 2010;59(4):213-21. doi: 10.5650/jos.59.213. PMID: 20299768.

17: Matsuda H, Morikawa T, Tao J, Ueda K, Yoshikawa M. Bioactive constituents of Chinese natural medicines. VII. Inhibitors of degranulation in RBL-2H3 cells and absolute stereostructures of three new diarylheptanoid glycosides from the bark of Myrica rubra. Chem Pharm Bull (Tokyo). 2002 Feb;50(2):208-15. doi: 10.1248/cpb.50.208. PMID: 11848211.

18: Ishida J, Kozuka M, Wang H, Konoshima T, Tokuda H, Okuda M, Yang Mou X, Nishino H, Sakurai N, Lee KH, Nagai M. Antitumor-promoting effects of cyclic diarylheptanoids on Epstein-Barr virus activation and two-stage mouse skin carcinogenesis. Cancer Lett. 2000 Oct 31;159(2):135-40. doi: 10.1016/s0304-3835(00)00538-3. PMID: 10996724.

19: Inoue T, Arai Y, Nagai M. [Diarylheptanoids in the bark of Myrica rubra Sieb. et Zucc]. Yakugaku Zasshi. 1984 Jan;104(1):37-41. Japanese. doi: 10.1248/yakushi1947.104.1_37. PMID: 6539823.