MedKoo Biosciences, Inc.
Tel:   +1-919-636-5577    Fax:   +1-919-980-4831    Email:   sales@medkoo.com
Search
Login Register
Search
MedKoo Cat#: 112131 | Name: Duclauxin
Featured

Description:

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

Duclauxin decreases proliferation of tumor cells in vitro.

Chemical Structure

Duclauxin
Duclauxin
CAS#1732-37-2

Theoretical Analysis

MedKoo Cat#: 112131

Name: Duclauxin

CAS#: 1732-37-2

Chemical Formula: C29H22O11

Exact Mass: 546.1162

Molecular Weight: 546.48

Elemental Analysis: C, 63.74; H, 4.06; O, 32.20

Price and Availability

Size Price Availability Quantity
500µg USD 450.00 2 Weeks
Bulk Inquiry
Buy Now
Add to Cart
Related CAS #
No Data
Synonym
Duclauxin; (9S)-Duclauxin; NSC258308; NSC-258308; NSC 258308;
IUPAC/Chemical Name
(8S,8aS,15aR,15bR,16S)-16-(acetyloxy)-8a,15a-dihydro-4,11-7H-8,15b-methano-1H,3H,12H-benzo[de]cyclohepta[1,2-g:3,4,5-d'e']bis[2]benzopyran-3,7,12,15(8H)-tetrone
InChi Key
WBQDAYWQELBEPU-FKKRYKJISA-N
InChi Code
InChI=1S/C29H22O11/c1-9-5-14(32)18-20-15(9)23(34)21-25(40-11(3)30)28(20,8-39-27(18)36)24-22(33)12-7-38-26(35)17-13(31)6-10(2)19(16(12)17)29(21,24)37-4/h5-7,21,24-25,31-32H,8H2,1-4H3/t21-,24+,25-,28-,29+/m0/s1
SMILES Code
OC1=CC(C)=C(C2=C1C(OC=C2C3=O)=O)[C@](OC)([C@]3([C@]45C6=C7C(OC5)=O)[H])[C@@]([H])(C(C6=C(C=C7O)C)=O)[C@@]4(OC(C)=O)[H]
Appearance
Solid powder
Purity
>95% (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

Preparing Stock Solutions

The following data is based on the product molecular weight 546.48 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: Shahid H, Cai T, Wang Y, Zheng C, Yang Y, Mao Z, Ding P, Shan T. Duclauxin Derivatives From Fungi and Their Biological Activities. Front Microbiol. 2021 Dec 22;12:766440. doi: 10.3389/fmicb.2021.766440. PMID: 35003004; PMCID: PMC8727740. 2: Sankawa U, Taguchi H, Ogihara Y, Shibata S. Biosynthesis of duclauxin. Tetrahedron Lett. 1966 Jun;25:2883-6. doi: 10.1016/s0040-4039(01)99879-x. PMID: 4164203. 3: Shibata S, Ogihara Y, Tokutake N, Tanaka O. Duclauxin, a metabolite of Penicillium duclauxi (Delacroix). Tetrahedron Lett. 1965 May;(18):1287-8. doi: 10.1016/s0040-4039(00)77197-8. PMID: 5844744. 4: Kawai K, Shiojiri H, Nakamaru T, Nozawa Y, Sugie S, Mori H, Kato T, Ogihara Y. Cytotoxicity and genotoxicity of xenoclauxin and desacetyl duclauxin from Penicillium duclauxii (Delacroix). Cell Biol Toxicol. 1985 Jan;1(2):1-10. doi: 10.1007/BF00717786. PMID: 3917122. 5: Chaudhary NK, Crombie A, Vuong D, Lacey E, Piggott AM, Karuso P. Talauxins: Hybrid Phenalenone Dimers from Talaromyces stipitatus. J Nat Prod. 2020 Apr 24;83(4):1051-1060. doi: 10.1021/acs.jnatprod.9b01066. Epub 2020 Mar 2. PMID: 32119543. 6: Cao P, Yang J, Miao CP, Yan Y, Ma YT, Li XN, Zhao LX, Huang SX. New duclauxamide from Penicillium manginii YIM PH30375 and structure revision of the duclauxin family. Org Lett. 2015 Mar 6;17(5):1146-9. doi: 10.1021/acs.orglett.5b00081. Epub 2015 Feb 19. PMID: 25695664. 7: Kawai K, Nozawa Y, Ito T, Yamanaka N. Effects of xanthomegnin and duclauxin on culture cells of murine leukemia and Ehrlich ascitic tumor. Res Commun Chem Pathol Pharmacol. 1982 Jun;36(3):429-38. PMID: 7122988. 8: Kuhr I, Fuska J, Sedmera P, Podojil M, Vokoun J, Vanĕk Z. An antitumor antibiotic produced by Penicillium stipitatum Thom; its identity with duclauxin. J Antibiot (Tokyo). 1973 Sep;26(9):535-6. doi: 10.7164/antibiotics.26.535. PMID: 4799788. 9: Samarasekera K, Hussein WM, Wu T, Salim AA, Capon RJ. Glyclauxins A-E: Dimeric Oxaphenalenone Aminoglycosides from an Australian Wasp Nest-Derived Fungus Talaromyces sp. CMB-MW102. J Nat Prod. 2023 Mar 24;86(3):517-525. doi: 10.1021/acs.jnatprod.2c01069. Epub 2023 Feb 17. PMID: 36800268. 10: Ogihara Y, Tanaka O, Shibata S. On the metabolites of penicillium duclauxi delacroix--3. The reactions of duclauxin with ammonia and primary amines. The structures of desacetylduclauxin, neoclauxin, xenoclauxin and cryptoclauxin. Tetrahedron Lett. 1966 Jun;25:2867-73. doi: 10.1016/s0040-4039(01)99876-4. PMID: 4164202. 11: Bryant FO, Cutler HG, Jacyno JM. Properties and cost effective method for production of the antitumor agent declauxin from sporulating Penicillium herquei. J Pharm Sci. 1993 Dec;82(12):1214-7. doi: 10.1002/jps.2600821206. PMID: 8308698. 12: Fuska Ia, Ivanitskaia LP, Makukho LV, Volkova LIa. Vliianie antibiotikov vermikulina PSX-1, bikaverina i duklauksina, vydelennykh iz gribov, na sintez nukleinovykh kislot v kletkakh nekotorykh opukholeĭ [The effects of the antibiotics vermiculin PSX-1, bicaverin and duclauxin, isolated from fungi, on nucleic acid synthesis in several tumors]. Antibiotiki. 1974 Oct;19(10):890-3. Russian. PMID: 4477948. 13: Gao SS, Zhang T, Garcia-Borràs M, Hung YS, Billingsley JM, Houk KN, Hu Y, Tang Y. Biosynthesis of Heptacyclic Duclauxins Requires Extensive Redox Modifications of the Phenalenone Aromatic Polyketide. J Am Chem Soc. 2018 Jun 6;140(22):6991-6997. doi: 10.1021/jacs.8b03705. Epub 2018 May 24. PMID: 29741874; PMCID: PMC6309916. 14: Frisvad JC, Filtenborg O, Samson RA, Stolk AC. Chemotaxonomy of the genus Talaromyces. Antonie Van Leeuwenhoek. 1990 Apr;57(3):179-89. doi: 10.1007/BF00403953. PMID: 2181929. 15: Fusková A, Proksa B, Fuska J. In vitro effect of duclauxin and derivatives of coumarin on nucleic acid and protein synthesis in Ehrlich's Ascites Carcinoma cells (EAC). Pharmazie. 1977 May;32(5):291-3. PMID: 896926. 16: Dethoup T, Manoch L, Kijjoa A, Nascimento MS, Puaparoj P, Silva AM, Eaton G, Herz W. Bacillisporins D and E, new oxyphenalenone dimers from Talaromyces bacillisporus. Planta Med. 2006 Aug;72(10):957-60. doi: 10.1055/s-2006-947188. Epub 2006 Aug 10. PMID: 16902873. 17: Wang M, Yang L, Feng L, Hu F, Zhang F, Ren J, Qiu Y, Wang Z. Verruculosins A-B, New Oligophenalenone Dimers from the Soft Coral-Derived Fungus Talaromyces verruculosus. Mar Drugs. 2019 Sep 2;17(9):516. doi: 10.3390/md17090516. PMID: 31480659; PMCID: PMC6780165. 18: Cooke RG, Edwards JM. Naturally occurring phenalenones and related compounds. Fortschr Chem Org Naturst. 1981;40:153-90. doi: 10.1007/978-3-7091-8611-4_4. PMID: 7016694. 19: Li Y, Kumar PS, Tan Q, Tan X, Yuan M, Luo J, He M. Diversity and chemical fingerprinting of endo-metabolomes from endophytes associated with Ampelopsis grossedentata (Hand.-Mazz.) W. T. Wang possessing antibacterial activity against multidrug resistant bacterial pathogens. J Infect Public Health. 2021 Dec;14(12):1917-1926. doi: 10.1016/j.jiph.2021.10.019. Epub 2021 Oct 25. PMID: 34728167. 20: Zang Y, Genta-Jouve G, Retailleau P, Escargueil A, Mann S, Nay B, Prado S. Talaroketals A and B, unusual bis(oxaphenalenone) spiro and fused ketals from the soil fungus Talaromyces stipitatus ATCC 10500. Org Biomol Chem. 2016 Mar 7;14(9):2691-7. doi: 10.1039/c5ob02657a. PMID: 26837531.