MedKoo Cat#: 574002 | Name: Cerebroside C
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Description:

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

Cerebroside C is a fungal metabolite and glycosphingolipid that induces production of the phytoalexin momilactone A when applied to wounded rice leaves, indicating that cerebroside C is an elicitor of the hypersensitive response in rice. Cerebroside C increases germination rate and reduces germination time in wheat seeds in a concentration-dependent manner at 4°C. It also increases root length, fresh weight, and dry weight of wheat seedlings when used at a concentration of 20 μg/ml at 4°C, indicating increased chilling tolerance.

Chemical Structure

Cerebroside C
Cerebroside C
CAS#98677-33-9

Theoretical Analysis

MedKoo Cat#: 574002

Name: Cerebroside C

CAS#: 98677-33-9

Chemical Formula: C43H79NO9

Exact Mass: 753.5755

Molecular Weight: 754.10

Elemental Analysis: C, 68.49; H, 10.56; N, 1.86; O, 19.09

Price and Availability

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1mg USD 1,050.00 2 Weeks
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Related CAS #
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Synonym
Cerebroside C
IUPAC/Chemical Name
(R,E)-2-hydroxy-N-((2S,3R,4E,8E)-3-hydroxy-9-methyl-1-(((2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)octadeca-4,8-dien-2-yl)octadec-3-enamide
InChi Key
QSPMXWIFLDIBGD-DDSPGNMTSA-N
InChi Code
InChI=1S/C43H79NO9/c1-4-6-8-10-12-13-14-15-16-17-18-20-22-26-31-37(47)42(51)44-35(33-52-43-41(50)40(49)39(48)38(32-45)53-43)36(46)30-27-23-25-29-34(3)28-24-21-19-11-9-7-5-2/h26-27,29-31,35-41,43,45-50H,4-25,28,32-33H2,1-3H3,(H,44,51)/b30-27+,31-26+,34-29+/t35-,36+,37+,38+,39+,40-,41+,43+/m0/s1
SMILES Code
O[C@H]1[C@H](O)[C@@H](CO)O[C@@H](OC[C@@H]([C@H](O)/C=C/CC/C=C(C)/CCCCCCCCC)NC([C@H](O)/C=C/CCCCCCCCCCCCCC)=O)[C@@H]1O
Appearance
Solid powder
Purity
>70% (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

Preparing Stock Solutions

The following data is based on the product molecular weight 754.10 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: Li HX, Xiao Y, Cao LL, Yan X, Li C, Shi HY, Wang JW, Ye YH. Cerebroside C increases tolerance to chilling injury and alters lipid composition in wheat roots. PLoS One. 2013 Sep 13;8(9):e73380. doi: 10.1371/journal.pone.0073380. PMID: 24058471; PMCID: PMC3772805. 2: Umemura K, Tanino S, Nagatsuka T, Koga J, Iwata M, Nagashima K, Amemiya Y. Cerebroside elicitor confers resistance to fusarium disease in various plant species. Phytopathology. 2004 Aug;94(8):813-8. doi: 10.1094/PHYTO.2004.94.8.813. PMID: 18943100. 3: Jiang T, Li T, Li J, Fu HZ, Pei YH, Lin WH. Cerebroside analogues from marine-derived fungus Aspergillus flavipes. J Asian Nat Prod Res. 2004 Dec;6(4):249-57. doi: 10.1080/1028602031000147384. PMID: 15621583. 4: Koga J, Yamauchi T, Shimura M, Ogawa N, Oshima K, Umemura K, Kikuchi M, Ogasawara N. Cerebrosides A and C, sphingolipid elicitors of hypersensitive cell death and phytoalexin accumulation in rice plants. J Biol Chem. 1998 Nov 27;273(48):31985-91. doi: 10.1074/jbc.273.48.31985. PMID: 9822670. 5: Talontsi FM, Nwemeguela Kenla TJ, Dittrich B, Douanla-Meli C, Laatsch H. Paeciloside A, a new antimicrobial and cytotoxic polyketide from Paecilomyces sp. strain CAFT156. Planta Med. 2012 Jun;78(10):1020-3. doi: 10.1055/s-0031-1298622. Epub 2012 Jun 12. PMID: 22692953. 6: Zhao JY, Liu Z, Sun SF, Liu YB. [Investigation on secondary metabolites of endophytic fungus Talaromyces purpurogenus hosted in Tylophora ovate]. Zhongguo Zhong Yao Za Zhi. 2020 Mar;45(6):1368-1373. Chinese. doi: 10.19540/j.cnki.cjcmm.20191204.201. PMID: 32281350. 7: Shu X, Zhang Y, Guan L, Chen Z, Huang M, Chen X, Yuan Y, Yuan C. [Antibacterial secondary metabolites of Clonostachys rosea, an endophytic fungus from Blumea balsamifera (L.) DC.]. Sheng Wu Gong Cheng Xue Bao. 2020 Aug 25;36(8):1650-1658. Chinese. doi: 10.13345/j.cjb.190555. PMID: 32924363. 8: Shushni MA, Azam F, Lindequist U. Oxasetin from Lophiostoma sp. of the Baltic Sea: identification, in silico binding mode prediction and antibacterial evaluation against fish pathogenic bacteria. Nat Prod Commun. 2013 Sep;8(9):1223-6. PMID: 24273851. 9: Zhang YG, Yuan WP, Xia XK, Jia AR, Liu X, Zhang MS, Liu CH. [The study of the secondary metabolites from fungus Paecilomyces sp]. Zhong Yao Cai. 2011 May;34(5):707-9. Chinese. PMID: 21954554.