Caulerpenyne | CAS# 70000-22-5

MedKoo Cat#: 412455 | Name: Caulerpenyne

Description:

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

Caulerpenyne is a biochemical from the marine algae Caulerpa taxifolia.

Chemical Structure

Caulerpenyne

CAS#70000-22-5

Theoretical Analysis

MedKoo Cat#: 412455

Name: Caulerpenyne

CAS#: 70000-22-5

Chemical Formula: C21H26O6

Exact Mass: 374.1729

Molecular Weight: 374.43

Elemental Analysis: C, 67.36; H, 7.00; O, 25.64

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 #

No Data

Synonym

Caulerpenyne

IUPAC/Chemical Name

1,6,10-Dodecatrien-8-yne-1,4-diol, 3-((acetyloxy)methylene)-7,11-dimethyl-, diacetate, (1E,3Z,4S,6E)-

InChi Key

INZBEAIXTUMDIW-WXBLODKZSA-N

InChi Code

InChI=1S/C21H26O6/c1-15(2)8-7-9-16(3)10-11-21(27-19(6)24)20(14-26-18(5)23)12-13-25-17(4)22/h8,10,12-14,21H,11H2,1-6H3/b13-12+,16-10+,20-14-/t21-/m0/s1

SMILES Code

C/C(C)=C\C#C/C(C)=C/C[C@H](OC(C)=O)C(/C=C/OC(C)=O)=C\OC(C)=O

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

More Info

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 374.43 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: Richter P, Schubert G, Schaible AM, Cavas L, Werz O, Pohnert G. Caulerpenyne and related bis-enol esters are novel-type inhibitors of human 5-lipoxygenase. ChemMedChem. 2014 Aug;9(8):1655-9. doi: 10.1002/cmdc.201402065. Epub 2014 Apr 11. PMID: 24729578. 2: Mozzachiodi R, Scuri R, Roberto M, Brunelli M. Caulerpenyne, a toxin from the seaweed Caulerpa taxifolia, depresses afterhyperpolarization in invertebrate neurons. Neuroscience. 2001;107(3):519-26. doi: 10.1016/s0306-4522(01)00365-7. PMID: 11719006. 3: Barbier P, Guise S, Huitorel P, Amade P, Pesando D, Briand C, Peyrot V. Caulerpenyne from Caulerpa taxifolia has an antiproliferative activity on tumor cell line SK-N-SH and modifies the microtubule network. Life Sci. 2001 Dec 14;70(4):415-29. doi: 10.1016/s0024-3205(01)01396-0. PMID: 11798011. 4: Cengiz S, Cavas L, Yurdakoc K, Pohnert G. The sesquiterpene caulerpenyne from Caulerpa spp. is a lipoxygenase inhibitor. Mar Biotechnol (NY). 2011 Apr;13(2):321-6. doi: 10.1007/s10126-010-9303-1. Epub 2010 Jun 22. PMID: 20567870. 5: Ciavatta ML, Lopez Gresa MP, Gavagnin M, Manzo E, Mollo E, D'Souza L, Cimino G. New caulerpenyne-derived metabolites of an Elysia sacoglossan from the South Indian coast. Molecules. 2006 Oct 25;11(10):808-16. doi: 10.3390/11100808. PMID: 17971757; PMCID: PMC6148565. 6: Bourdron J, Barbier P, Allegro D, Villard C, Lafitte D, Commeiras L, Parrain JL, Peyrot V. Caulerpenyne binding to tubulin: structural modifications by a non conventional pharmacological agent. Med Chem. 2009 Mar;5(2):182-90. doi: 10.2174/157340609787582891. PMID: 19275717. 7: Jung V, Thibaut T, Meinesz A, Pohnert G. Comparison of the wound-activated transformation of caulerpenyne by invasive and noninvasive Caulerpa species of the Mediterranean. J Chem Ecol. 2002 Oct;28(10):2091-105. doi: 10.1023/a:1020710230532. PMID: 12474902. 8: Marić P, Ahel M, Senta I, Terzić S, Mikac I, Žuljević A, Smital T. Effect- directed analysis reveals inhibition of zebrafish uptake transporter Oatp1d1 by caulerpenyne, a major secondary metabolite from the invasive marine alga Caulerpa taxifolia. Chemosphere. 2017 May;174:643-654. doi: 10.1016/j.chemosphere.2017.02.007. Epub 2017 Feb 2. PMID: 28199941. 9: Brunelli M, Garcia-Gil M, Mozzachiodi R, Roberto M, Scuri R, Traina G, Zaccardi ML. Neurotoxic effects of caulerpenyne. Prog Neuropsychopharmacol Biol Psychiatry. 2000 Aug;24(6):939-54. doi: 10.1016/s0278-5846(00)00112-3. PMID: 11041536. 10: Sureda A, Box A, Deudero S, Pons A. Reciprocal effects of caulerpenyne and intense herbivorism on the antioxidant response of Bittium reticulatum and Caulerpa taxifolia. Ecotoxicol Environ Saf. 2009 Mar;72(3):795-801. doi: 10.1016/j.ecoenv.2007.12.007. Epub 2008 Jan 29. PMID: 18234333.

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