Anthricin | CAS# 19186-35-7 | antitumor constituent

MedKoo Cat#: 413538 | Name: Anthricin

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Description:

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

Anthricin (deoxypodophyllotoxin) is a major lignan in Anthriscus sylvestris (L.) Hoffm and has many bioactivities such as antiproliferative, antitumor, anti-platelet aggregation, antiviral, anti-inflammatory and liver protective actions. Numerous studies have reported the anticancer effect of anthricin on various cancer cells, such as gastric and breast cancer, cervical carcinoma and lung cancer, through G2/M cell cycle arrest, microtubule formation inhibition, and caspase-dependent apoptosis.

Chemical Structure

Anthricin

CAS#19186-35-7

Theoretical Analysis

MedKoo Cat#: 413538

Name: Anthricin

CAS#: 19186-35-7

Chemical Formula: C22H22O7

Exact Mass: 398.1366

Molecular Weight: 398.41

Elemental Analysis: C, 66.32; H, 5.57; O, 28.11

Price and Availability

Size	Price	Availability	Quantity
10mg	USD 250.00	2 Weeks
25mg	USD 500.00	2 Weeks

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Related CAS #

No Data

Synonym

Anthricin; AS2-3; AS-2-3; AS 2-3; Deoxypodophyllotoxin; (–)-Deoxypodophyllotoxin; 4-Deoxypodophyllotoxin; DPT; RD4-6266; RD46266; RD4 6266

IUPAC/Chemical Name

Furo(3',4':6,7)naphtho(2,3-d)-1,3-dioxol-6(5aH)-one, 5,8,8a,9-tetrahydro-5-(3,4,5-trimethoxyphenyl)-, (5R,5aR,8aR)-

InChi Key

ZGLXUQQMLLIKAN-SVIJTADQSA-N

InChi Code

InChI=1S/C22H22O7/c1-24-17-6-12(7-18(25-2)21(17)26-3)19-14-8-16-15(28-10-29-16)5-11(14)4-13-9-27-22(23)20(13)19/h5-8,13,19-20H,4,9-10H2,1-3H3/t13-,19+,20-/m0/s1

SMILES Code

O=C1OC[C@]2([H])CC3=C(C=C4OCOC4=C3)[C@@H](C5=CC(OC)=C(OC)C(OC)=C5)[C@]21[H]

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

To be determined

Shelf Life

>2 years if stored properly

Drug Formulation

To be determined

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

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	Solvent	mg/mL	mM
Solubility
	To be determined	0.0	0.00

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 398.41 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: Park BR, Lee SA, Moon SM, Kim CS. Anthricin‑induced caspase‑dependent apoptosis through IGF1R/PI3K/AKT pathway inhibition in A549 human non‑small lung cancer cells. Oncol Rep. 2018 Jun;39(6):2769-2776. doi: 10.3892/or.2018.6333. Epub 2018 Mar 27. PMID: 29620219. 2: Esmeeta A, Adhikary S, Dharshnaa V, Swarnamughi P, Ummul Maqsummiya Z, Banerjee A, Pathak S, Duttaroy AK. Plant-derived bioactive compounds in colon cancer treatment: An updated review. Biomed Pharmacother. 2022 Sep;153:113384. doi: 10.1016/j.biopha.2022.113384. Epub 2022 Jul 9. PMID: 35820317. 3: Jung CH, Kim H, Ahn J, Jung SK, Um MY, Son KH, Kim TW, Ha TY. Anthricin Isolated from Anthriscus sylvestris (L.) Hoffm. Inhibits the Growth of Breast Cancer Cells by Inhibiting Akt/mTOR Signaling, and Its Apoptotic Effects Are Enhanced by Autophagy Inhibition. Evid Based Complement Alternat Med. 2013;2013:385219. doi: 10.1155/2013/385219. Epub 2013 May 29. PMID: 23818925; PMCID: PMC3681310. 4: Inamori Y, Kato Y, Kubo M, Baba K, Ishida T, Nomoto K, Kozawa M. The biological actions of deoxypodophyllotoxin (anthricin). I. Physiological activities and conformational analysis of deoxypodophyllotoxin. Chem Pharm Bull (Tokyo). 1985 Feb;33(2):704-9. doi: 10.1248/cpb.33.704. PMID: 4017115. 5: Yamamoto D, Ohishi H, Kozawa M, Inamori Y, Ishida T, Inoue M. Study on conformations--biological activities relationships for podophyllotoxin analogues based on crystal structure of deoxypodophyllotoxin (anthricin). Chem Pharm Bull (Tokyo). 1988 Sep;36(9):3239-47. doi: 10.1248/cpb.36.3239. PMID: 3240529. 6: Kim HY, Lee SG, Oh TJ, Lim SR, Kim SH, Lee HJ, Kim YS, Choi HK. Antiproliferative and Apoptotic Activity of Chamaecyparis obtusa Leaf Extract against the HCT116 Human Colorectal Cancer Cell Line and Investigation of the Bioactive Compound by Gas Chromatography-Mass Spectrometry-Based Metabolomics. Molecules. 2015 Oct 2;20(10):18066-82. doi: 10.3390/molecules201018066. PMID: 26445036; PMCID: PMC6332506. 7: Ikeda R, Nagao T, Okabe H, Nakano Y, Matsunaga H, Katano M, Mori M. Antiproliferative constituents in umbelliferae plants. III. Constituents in the root and the ground part of Anthriscus sylvestris Hoffm. Chem Pharm Bull (Tokyo). 1998 May;46(5):871-4. doi: 10.1248/cpb.46.871. PMID: 9621422. 8: Lin CX, Son MJ, Ju HK, Moon TC, Lee E, Kim SH, Kim MJ, Son JK, Lee SH, Chang HW. Deoxypodophyllotoxin, a naturally occurring lignan, inhibits the passive cutaneous anaphylaxis reaction. Planta Med. 2004 May;70(5):474-6. doi: 10.1055/s-2004-818981. PMID: 15124098. 9: Su BN, Jones WP, Cuendet M, Kardono LB, Ismail R, Riswan S, Fong HH, Farnsworth NR, Pezzuto JM, Kinghorn AD. Constituents of the stems of Macrococculus pomiferus and their inhibitory activities against cyclooxygenases-1 and -2. Phytochemistry. 2004 Nov;65(21):2861-6. doi: 10.1016/j.phytochem.2004.08.007. PMID: 15501253. 10: Lee SH, Son MJ, Ju HK, Lin CX, Moon TC, Choi HG, Son JK, Chang HW. Dual inhibition of cyclooxygenases-2 and 5-lipoxygenase by deoxypodophyllotoxin in mouse bone marrow-derived mast cells. Biol Pharm Bull. 2004 Jun;27(6):786-8. doi: 10.1248/bpb.27.786. PMID: 15187418. 11: Chen H, Jiang HZ, Li YC, Wei GQ, Geng Y, Ma CY. Antitumor constituents from Anthriscus sylvestris (L.) Hoffm. Asian Pac J Cancer Prev. 2014;15(6):2803-7. doi: 10.7314/apjcp.2014.15.6.2803. PMID: 24761904.

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Harpagoside