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MedKoo Cat#: 463821 | Name: Americanin A

Description:

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

Americanin A natural thrombin inhibitor, suppressing melanin synthesis, regulating the ATM/ATR signaling pathway and the Skp2-p27 axis in human colon cancer cells.

Chemical Structure

Americanin A
Americanin A
CAS#69506-79-2

Theoretical Analysis

MedKoo Cat#: 463821

Name: Americanin A

CAS#: 69506-79-2

Chemical Formula: C18H16O6

Exact Mass: 328.0947

Molecular Weight: 328.32

Elemental Analysis: C, 65.85; H, 4.91; O, 29.24

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
Americanin A; Americanin-A;
IUPAC/Chemical Name
(E)-3-((2S,3S)-2-(3,4-dihydroxyphenyl)-3-(hydroxymethyl)-2,3-dihydrobenzo[b][1,4]dioxin-6-yl)acrylaldehyde
InChi Key
NTXXGPYGMQQSML-QLJMBOKNSA-N
InChi Code
InChI=1S/C18H16O6/c19-7-1-2-11-3-6-15-16(8-11)23-17(10-20)18(24-15)12-4-5-13(21)14(22)9-12/h1-9,17-18,20-22H,10H2/b2-1+/t17-,18-/m0/s1
SMILES Code
O=C/C=C/C1=CC=C(O[C@@H](C2=CC=C(O)C(O)=C2)[C@H](CO)O3)C3=C1
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 328.32 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: De La Cruz-Sánchez NG, Gómez-Rivera A, Alvarez-Fitz P, Ventura-Zapata E, Pérez-García MD, Avilés-Flores M, Gutiérrez-Román AS, González-Cortazar M. Antibacterial activity of Morinda citrifolia Linneo seeds against Methicillin- Resistant Staphylococcus spp. Microb Pathog. 2019 Mar;128:347-353. doi: 10.1016/j.micpath.2019.01.030. Epub 2019 Jan 23. PMID: 30682527. 2: Shin Y, Jang EJ, Park HJ, Hong JY, Kang SS, Lee SK. Suppression of melanin synthesis by Americanin A in melan-a cells via regulation of microphthalmia- associated transcription factor. Exp Dermatol. 2016 Aug;25(8):646-7. doi: 10.1111/exd.13013. Epub 2016 Jun 1. PMID: 26997427. 3: Jung C, Hong JY, Bae SY, Kang SS, Park HJ, Lee SK. Antitumor Activity of Americanin A Isolated from the Seeds of Phytolacca americana by Regulating the ATM/ATR Signaling Pathway and the Skp2-p27 Axis in Human Colon Cancer Cells. J Nat Prod. 2015 Dec 24;78(12):2983-93. doi: 10.1021/acs.jnatprod.5b00743. Epub 2015 Nov 23. PMID: 26595875. 4: Pazar E, Akgül Y. Chemical composition of the endocarps of fruits of Styrax officinalis L. Nat Prod Res. 2015;29(15):1466-8. doi: 10.1080/14786419.2014.1003063. Epub 2015 Jan 23. PMID: 25613173. 5: Masuda M, Murata K, Naruto S, Uwaya A, Isami F, Matsuda H. Matrix metalloproteinase-1 inhibitory activities of Morinda citrifolia seed extract and its constituents in UVA-irradiated human dermal fibroblasts. Biol Pharm Bull. 2012;35(2):210-5. doi: 10.1248/bpb.35.210. PMID: 22293351. 6: Masuda M, Itoh K, Murata K, Naruto S, Uwaya A, Isami F, Matsuda H. Inhibitory effects of Morinda citrifolia extract and its constituents on melanogenesis in murine B16 melanoma cells. Biol Pharm Bull. 2012;35(1):78-83. doi: 10.1248/bpb.35.78. PMID: 22223341. 7: Masuda M, Murata K, Fukuhama A, Naruto S, Fujita T, Uwaya A, Isami F, Matsuda H. Inhibitory effects of constituents of Morinda citrifolia seeds on elastase and tyrosinase. J Nat Med. 2009 Jul;63(3):267-73. doi: 10.1007/s11418-009-0328-6. Epub 2009 Mar 24. PMID: 19308654. 8: Schwarz B, Hofmann T. Identification of novel orosensory active molecules in cured vanilla Beans (Vanilla planifolia). J Agric Food Chem. 2009 May 13;57(9):3729-37. doi: 10.1021/jf900086m. PMID: 19298044. 9: Lin CF, Ni CL, Huang YL, Sheu SJ, Chen CC. Lignans and anthraquinones from the fruits of Morinda citrifolia. Nat Prod Res. 2007 Nov;21(13):1199-204. doi: 10.1080/14786410601132451. PMID: 17987501. 10: Shoeb M, MacManus SM, Kumarasamy Y, Jaspars M, Nahar L, Thoo-Lin PK, Nazemiyeh H, Sarker SD. Americanin, a bioactive dibenzylbutyrolactone lignan, from the seeds of Centaurea americana. Phytochemistry. 2006 Nov;67(21):2370-5. doi: 10.1016/j.phytochem.2006.08.012. Epub 2006 Sep 22. PMID: 16996096. 11: Su BN, Pawlus AD, Jung HA, Keller WJ, McLaughlin JL, Kinghorn AD. Chemical constituents of the fruits of Morinda citrifolia (Noni) and their antioxidant activity. J Nat Prod. 2005 Apr;68(4):592-5. doi: 10.1021/np0495985. PMID: 15844957. 12: Kamiya K, Tanaka Y, Endang H, Umar M, Satake T. Chemical constituents of Morinda citrifolia fruits inhibit copper-induced low-density lipoprotein oxidation. J Agric Food Chem. 2004 Sep 22;52(19):5843-8. doi: 10.1021/jf040114k. PMID: 15366830. 13: Waibel R, Benirschke G, Benirschke M, Achenbach H. Sesquineolignans and other constituents from the seeds of Joannesia princeps. Phytochemistry. 2003 Mar;62(5):805-11. doi: 10.1016/s0031-9422(02)00357-6. PMID: 12620334. 14: Zhu K, Bowman AS, Brigham DL, Essenberg RC, Dillwith JW, Sauer JR. Isolation and characterization of americanin, a specific inhibitor of thrombin, from the salivary glands of the lone star tick Amblyomma americanum (L.). Exp Parasitol. 1997 Sep;87(1):30-8. doi: 10.1006/expr.1997.4175. PMID: 9287955. 15: Fukuyama Y, Hasegawa T, Toda M, Kodama M, Okazaki H. Structures of americanol A and isoamericanol A having a neurotrophic property from the seeds of Phytolacca americana. Chem Pharm Bull (Tokyo). 1992 Jan;40(1):252-4. doi: 10.1248/cpb.40.252. PMID: 1576680. 16: Tanaka H, Kato I, Ito K. Total synthesis of neolignans, americanin A and isoamericanin A. Chem Pharm Bull (Tokyo). 1987 Sep;35(9):3603-8. doi: 10.1248/cpb.35.3603. PMID: 3435966.