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S3523

Sigma-Aldrich

Surfactin

from Bacillus subtilis, ≥98.0% (HPLC)

Synonym(s):

surfactin C

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$282.00
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10 MG
$282.00
50 MG
$966.00

About This Item

Empirical Formula (Hill Notation):
C53H93N7O13
CAS Number:
24730-31-2
Molecular Weight:
1036.34
UNSPSC Code:
51102829
PubChem Substance ID:
24899562
NACRES:
NA.85

$282.00

In StockDetails

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biological source

Bacillus subtilis

Quality Level

200

description

zwitterionic

assay

≥98.0% (HPLC)

form

powder

storage condition

(Keep container tightly closed in a dry and well-ventilated place. Keep in a dry place.)

color

white to faint yellow

CMC

7.5-20 μmol/L (depending on methods)

solubility

ethanol: soluble 10 mg/mL

antibiotic activity spectrum

Gram-negative bacteria
Gram-positive bacteria
fungi
mycoplasma
neoplastics
viruses

mode of action

cell membrane | interferes

storage temp.

2-8°C

SMILES string

CC(C)CCCCCCCCC[C@@H]1CC(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@H](CC(C)C)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@H](CC(C)C)C(=O)N[C@@H](CC(C)C)C(=O)O1

InChI

1S/C53H93N7O13/c1-30(2)20-18-16-14-13-15-17-19-21-36-28-43(61)54-37(22-23-44(62)63)47(66)55-38(24-31(3)4)48(67)57-40(26-33(7)8)51(70)60-46(35(11)12)52(71)58-41(29-45(64)65)50(69)56-39(25-32(5)6)49(68)59-42(27-34(9)10)53(72)73-36/h30-42,46H,13-29H2,1-12H3,(H,54,61)(H,55,66)(H,56,69)(H,57,67)(H,58,71)(H,59,68)(H,60,70)(H,62,63)(H,64,65)/t36-,37+,38+,39-,40-,41+,42+,46+/m1/s1

InChI key

NJGWOFRZMQRKHT-WGVNQGGSSA-N

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General description

Chemical structure: peptide

Application

Surfactin is used as a surfactant to mediate flux of mono-and divalent cations, such as calcium, across lipid bilayer membranes. It is also used to study antitumor activity, activity against enveloped viruses, activity against the protoplast of Bacillus megaterium and the activity against Mycoplasma[1].

Biochem/physiol Actions

Surfactin is a lipopeptide antibiotic that is composed of one β-hydroxy fatty acid, which has a long fatty acid moiety, and seven amino acids. Three of them have D configurations. It is a powerful biosurfactant that causes lysis of erythrocytes and bacteria. It is also a clotting inhibitor. Surfactin is thought to disrupt or disintegrate membranes via physicochemical interaction with the membranes[1].

Other Notes

Keep container tightly closed in a dry and well-ventilated place. Keep in a dry place.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
0000422734
0000422734
0000411103
0000411103
0000369072

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M M Nakano et al.
Journal of bacteriology, 170(12), 5662-5668 (1988-12-01)
Surfactin is a lipopeptide antibiotic produced by the cells of Bacillus subtilis ATCC 21332. A genetic locus responsible for surfactin production (sfp) was transferred from ATCC 21332 to JH642, a derivative of the standard B. subtilis 168. To study the
Sun Young Park et al.
Toxicology and applied pharmacology, 268(1), 68-78 (2013-01-31)
Surfactin, one of the most powerful biosurfactants, is a bacterial cyclic lipopeptide. Here, we investigated the anti-neuroinflammatory properties of surfactin in lipoteichoic acid (LTA)-stimulated BV-2 microglial cells. Surfactin significantly inhibited excessive production of the pro-inflammatory mediators TNF-α, IL-1β, IL-6, monocyte
F Alvarez et al.
Journal of applied microbiology, 112(1), 159-174 (2011-10-25)
This work was conducted to identify the antifungal compounds produced by two previously isolated Bacillus sp. strains: ARP(2) 3 and MEP(2) 18. Both strains were subjected to further analysis to determine their taxonomic position and to identify the compounds responsible
David J Gonzalez et al.
Microbiology (Reading, England), 157(Pt 9), 2485-2492 (2011-07-02)
Microbial competition exists in the general environment, such as soil or aquatic habitats, upon or within unicellular or multicellular eukaryotic life forms. The molecular actions that govern microbial competition, leading to niche establishment and microbial monopolization, remain undetermined. The emerging
Helen Y Fan et al.
Biochimica et biophysica acta, 1838(9), 2306-2312 (2014-03-19)
The effective charge of membrane-active molecules such as the fungicidal lipopeptide surfactin (SF) is a crucial property governing solubility, membrane partitioning, and membrane permeability. We present zeta potential measurements of liposomes to measure the effective charge as well as membrane
View All Related Papers

Questions

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  1. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer

    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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  2. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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