Laminaran
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MedKoo CAT#: 598247

CAS#: 9008-22-4

Description: Laminaran is a beta-(1-3)-linked D-glucan with .BETA.-(1-6) linkages. The major M-series contains 20-30 glucosyl residues linked to terminal mannitol, and a minor G-series with 22-28 glucosyl residues. There is a 3 to 1 ratio of M-series to G-series molecules. There is an average of 1.3 branches per molecule.


Chemical Structure

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Laminaran
CAS# 9008-22-4

Theoretical Analysis

MedKoo Cat#: 598247
Name: Laminaran
CAS#: 9008-22-4
Chemical Formula: C18H32O16
Exact Mass: 504.169
Molecular Weight: 504.43
Elemental Analysis: C, 42.86; H, 6.39; O, 50.75

Price and Availability

Size Price Availability Quantity
500.0mg USD 250.0 2 Weeks
1.0g USD 450.0 2 Weeks
2.0g USD 750.0 2 Weeks
5.0g USD 1250.0 2 Weeks
10.0g USD 1950.0 2 Weeks
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Synonym: Laminaran; Iodus 40; beta-1,3-Glucan;

IUPAC/Chemical Name: (3R,4S,5R,6R)-4-(((3R,4S,5R,6R)-3,5-dihydroxy-6-(hydroxymethyl)-4-(((3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)tetrahydro-2H-pyran-2-yl)oxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-2,3,5-triol

InChi Key: DBTMGCOVALSLOR-VPNXCSTESA-N

InChi Code: InChI=1S/C18H32O16/c19-1-4-7(22)10(25)11(26)17(31-4)34-15-9(24)6(3-21)32-18(13(15)28)33-14-8(23)5(2-20)30-16(29)12(14)27/h4-29H,1-3H2/t4-,5-,6-,7-,8-,9-,10+,11-,12-,13-,14+,15+,16?,17?,18?/m1/s1

SMILES Code: OC[C@H]1OC([C@@H]([C@H]([C@@H]1O)O)O)O[C@H]2[C@@H]([C@H](OC([C@@H]2O)O[C@@H]3[C@H](C(O[C@@H]([C@H]3O)CO)O)O)CO)O

Appearance: Solid powder

Purity: Unknown (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: DMSO (Slightly, Heated), Water (Slightly)

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 504.43 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.

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: Ayoub A, Pereira JM, Rioux LE, Turgeon SL, Beaulieu M, Moulin VJ. Role of seaweed laminaran from Saccharina longicruris on matrix deposition during dermal tissue-engineered production. Int J Biol Macromol. 2015 Apr;75:13-20. doi: 10.1016/j.ijbiomac.2015.01.017. Epub 2015 Jan 17. PubMed PMID: 25603140.

2: Kuda T, Kosaka M, Hirano S, Kawahara M, Sato M, Kaneshima T, Nishizawa M, Takahashi H, Kimura B. Effect of sodium-alginate and laminaran on Salmonella Typhimurium infection in human enterocyte-like HT-29-Luc cells and BALB/c mice. Carbohydr Polym. 2015 Jul 10;125:113-9. doi: 10.1016/j.carbpol.2015.01.078. Epub 2015 Feb 26. PubMed PMID: 25857966.

3: Menshova RV, Ermakova SP, Anastyuk SD, Isakov VV, Dubrovskaya YV, Kusaykin MI, Um BH, Zvyagintseva TN. Structure, enzymatic transformation and anticancer activity of branched high molecular weight laminaran from brown alga Eisenia bicyclis. Carbohydr Polym. 2014 Jan;99:101-9. doi: 10.1016/j.carbpol.2013.08.037. Epub 2013 Aug 21. PubMed PMID: 24274485.

4: Jin W, Zhang W, Wang J, Ren S, Song N, Duan D, Zhang Q. Characterization of laminaran and a highly sulfated polysaccharide from Sargassum fusiforme. Carbohydr Res. 2014 Feb 19;385:58-64. doi: 10.1016/j.carres.2013.12.009. Epub 2013 Dec 18. PubMed PMID: 24413558.

5: An C, Kuda T, Yazaki T, Takahashi H, Kimura B. FLX pyrosequencing analysis of the effects of the brown-algal fermentable polysaccharides alginate and laminaran on rat cecal microbiotas. Appl Environ Microbiol. 2013 Feb;79(3):860-6. doi: 10.1128/AEM.02354-12. Epub 2012 Nov 26. PubMed PMID: 23183985; PubMed Central PMCID: PMC3568576.

6: Nakata T, Kyoui D, Takahashi H, Kimura B, Kuda T. Inhibitory effects of laminaran and alginate on production of putrefactive compounds from soy protein by intestinal microbiota in vitro and in rats. Carbohydr Polym. 2016 Jun 5;143:61-9. doi: 10.1016/j.carbpol.2016.01.064. Epub 2016 Feb 4. PubMed PMID: 27083344.

7: Rioux LE, Turgeon SL, Beaulieu M. Structural characterization of laminaran and galactofucan extracted from the brown seaweed Saccharina longicruris. Phytochemistry. 2010 Sep;71(13):1586-95. doi: 10.1016/j.phytochem.2010.05.021. Epub 2010 Jul 3. PubMed PMID: 20599236.

8: Nobe R, Sakakibara Y, Fukuda N, Yoshida N, Ogawa K, Suiko M. Purification and characterization of laminaran hydrolases from Trichoderma viride. Biosci Biotechnol Biochem. 2003 Jun;67(6):1349-57. PubMed PMID: 12843664.

9: El-Boshy ME, El-Ashram AM, Abdelhamid FM, Gadalla HA. Immunomodulatory effect of dietary Saccharomyces cerevisiae, beta-glucan and laminaran in mercuric chloride treated Nile tilapia (Oreochromis niloticus) and experimentally infected with Aeromonas hydrophila. Fish Shellfish Immunol. 2010 May-Jun;28(5-6):802-8. doi: 10.1016/j.fsi.2010.01.017. Epub 2010 Feb 6. PubMed PMID: 20139003.

10: Iida A, Ouchi S, Oda T, Aketagawa J, Ito Y, Takizawa Y, Tomita M, Hayashi M. Changes of Absorptive and Secretory Transporting System of (1 → 3) β-D-glucan Based on Efflux Transporter in Indomethacin-induced Rat. Eur J Drug Metab Pharmacokinet. 2015 Mar;40(1):29-38. doi: 10.1007/s13318-014-0174-0. Epub 2014 Feb 11. PubMed PMID: 24515798.

11: Frecer V, Rizzo R, Miertus S. Molecular dynamics study on the conformational stability of laminaran oligomers in various solvents. Biomacromolecules. 2000 Spring;1(1):91-9. PubMed PMID: 11709848.

12: Tanaka S, Aketagawa J, Takahashi S, Shibata Y, Tsumuraya Y, Hashimoto Y. Inhibition of high-molecular-weight-(1-->3)-beta-D-glucan-dependent activation of a limulus coagulation factor G by laminaran oligosaccharides and curdlan degradation products. Carbohydr Res. 1993 May 21;244(1):115-27. PubMed PMID: 8339297.

13: Contour-Galcera MO, Guillot JM, Ortiz-Mellet C, Pflieger-Carrara F, Defaye J, Gelas J. Synthesis of sulfur-linked analogues of nigerose, laminarabiose, laminaratriose, gentiobiose, gentiotriose, and laminaran trisaccharide Y. Carbohydr Res. 1996 Feb 7;281(1):99-118. PubMed PMID: 8839179.

14: Murata K. Suppression of lipid synthesis in cultured aortic cells by laminaran sulfate. J Atheroscler Res. 1969 Nov-Dec;10(3):371-8. PubMed PMID: 5364086.

15: Menshova RV, Anastyuk SD, Ermakova SP, Shevchenko NM, Isakov VI, Zvyagintseva TN. Structure and anticancer activity in vitro of sulfated galactofucan from brown alga Alaria angusta. Carbohydr Polym. 2015 Nov 5;132:118-25. doi: 10.1016/j.carbpol.2015.06.020. Epub 2015 Jun 14. PubMed PMID: 26256332.

16: Shibata Y. Enzymatic hydrolysis of glucans containing beta-1, 3- and beta-1, 6-linkages. 3. Gibberella beta-1, 6-glucan 6-glucanohydrolase operative in the selective hydrolysis of beta-1, 3-glucosidic linkages in Eisemia laminaran. J Biochem. 1974 Jan;75(1):85-92. PubMed PMID: 4826543.

17: Maeda M, Nishizawa K. Fine structure of laminaran of Eisenia bicyclis. J Biochem. 1968 Feb;63(2):199-206. PubMed PMID: 4299375.

18: Wan-Mohtar WA, Young L, Abbott GM, Clements C, Harvey LM, McNeil B. Antimicrobial Properties and Cytotoxicity of Sulfated (1,3)-β-D-Glucan from the Mycelium of the Mushroom Ganoderma lucidum. J Microbiol Biotechnol. 2016 Jun 28;26(6):999-1010. doi: 10.4014/jmb.1510.10018. PubMed PMID: 26907757.

19: Tontini M, Romano MR, Proietti D, Balducci E, Micoli F, Balocchi C, Santini L, Masignani V, Berti F, Costantino P. Preclinical studies on new proteins as carrier for glycoconjugate vaccines. Vaccine. 2016 Jul 29;34(35):4235-4242. doi: 10.1016/j.vaccine.2016.06.039. Epub 2016 Jun 24. Erratum in: Vaccine. 2017 May 2;35(19):2612. PubMed PMID: 27317455.

20: Nelson TE, Lewis BA. Separation and characterization of the soluble and insoluble components of insoluble laminaran. Carbohydr Res. 1974 Mar;33(1):63-74. PubMed PMID: 4363664.

Laminaran

500.0mg / USD 250.0