SarMentine
- Product Name
- SarMentine
- CAS No.
- 78910-33-5
- Chemical Name
- SarMentine
- Synonyms
- SarMentine;2,4-Decadienoic acid pyrrolidide;1-(1-Oxo-2,4-decadienyl)pyrrolidine;(E,E)-1-(oxo-2,4-decadienyl) pyrrolidine;(2E,4E)-1-(Pyrrolidin-1-yl)deca-2,4-dien-1-one;2,4-Decadien-1-one, 1-(1-pyrrolidinyl)-, (2E,4E)-
- CBNumber
- CB62251880
- Molecular Formula
- C14H23NO
- Formula Weight
- 221.34
- MOL File
- 78910-33-5.mol
SarMentine Property
- Boiling point:
- 373.0±9.0 °C(Predicted)
- Density
- 0.961±0.06 g/cm3(Predicted)
- storage temp.
- under inert gas (nitrogen or Argon) at 2-8°C
- solubility
- Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
- pka
- -0.87±0.20(Predicted)
- form
- Solid
- color
- Light Orange to Brown
- InChI
- InChI=1S/C14H23NO/c1-2-3-4-5-6-7-8-11-14(16)15-12-9-10-13-15/h6-8,11H,2-5,9-10,12-13H2,1H3/b7-6+,11-8+
- InChIKey
- BFZBGTMIBOQWBA-HRCSPUOPSA-N
- SMILES
- C(N1CCCC1)(=O)/C=C/C=C/CCCCC
- LogP
- 3.264 (est)
- EPA Substance Registry System
- 2,4-Decadien-1-one, 1-(1-pyrrolidinyl)-, (2E,4E)- (78910-33-5)
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Warning
- Hazard statements
-
H302Harmful if swallowed
H315Causes skin irritation
H319Causes serious eye irritation
H332Harmful if inhaled
H335May cause respiratory irritation
- Precautionary statements
-
P261Avoid breathing dust/fume/gas/mist/vapours/spray.
P280Wear protective gloves/protective clothing/eye protection/face protection.
P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
N-Bromosuccinimide Price
- Product number
- S141600
- Product name
- Sarmentine
- Packaging
- 10mg
- Price
- $150
- Updated
- 2021/12/16
- Product number
- CHM0388160
- Product name
- (2E,4E)-1-(PYRROLIDIN-1-YL)DECA-2,4-DIEN-1-ONE
- Purity
- 95.00%
- Packaging
- 5MG
- Price
- $505.98
- Updated
- 2021/12/16
- Product number
- 42197
- Product name
- Sarmentine
- Packaging
- 10mg
- Price
- $650
- Updated
- 2021/12/16
- Product number
- A380844
- Product name
- (2E,4E)-1-(Pyrrolidin-1-yl)deca-2,4-dien-1-one
- Purity
- 98%
- Packaging
- 100mg
- Price
- $58
- Updated
- 2021/12/16
- Product number
- CD11056582
- Product name
- (2E,4E)-1-(Pyrrolidin-1-yl)deca-2,4-dien-1-one
- Purity
- 98%
- Packaging
- 250mg
- Price
- $79
- Updated
- 2021/12/16
SarMentine Chemical Properties,Usage,Production
Description
Sarmentine: a contact herbicide with broad-spectrum activity.
Sarmentine, 1-(1-pyrrolidinyl)-(2E,4E)-2,4-decadien-1-one, is a natural amide isolated from the fruits of Piper species. It has several biological properties, including antiplasmodial, antimycobacterial, antituberculosis activity, and antiplatelet aggregation. Sarmentine acts as a contact herbicide with broad-spectrum activity similarly to herbicidal soaps, such as nonanoic acid (pelargonic acid) or decanoic acid[1].
Chemical Properties
Light Orange to Brown Low Melting Solid
Uses
Sarmentine is used for controlling plant pests.
Definition
ChEBI: 1-[(2E,4E)-2,4-decadienoyl]pyrrolidine is a N-acylpyrrolidine. It has a role as a metabolite.
Mode of action
In cucumber cotyledon disc assays, sarmentine induced rapid light-independent loss of membrane integrity at 100 μM or higher concentration, whereas 3 mM pelargonic acid was required for a similar effect. Sarmentine was between 10 and 30 times more active than pelargonic acid on wild mustard, velvetleaf, redroot pigweed and crabgrass. Additionally, the potency of 30 μM sarmentine was greatly stimulated by light, suggesting that this natural product may also interfere with photosynthetic processes. Sarmentine also acted as an inhibitor of photosystem II (PSII) on isolated thylakoid membranes by competing for the binding site of plastoquinone. This can be attributed in part to structural similarities between herbicides like sarmentine and diuron. While this mechanism of action accounts for the light stimulation of the activity of sarmentine, it does not account for its ability to destabilize membranes in darkness. In this respect, sarmentine has some structural similarity to crotonoyl-CoA, the substrate of enoyl-ACP reductase, a key enzyme in the early steps of fatty acid synthesis. Inhibitors of this enzyme, such as triclosan, cause rapid loss of membrane integrity in the dark. Sarmentine inhibited the activity of enoyl-ACP reductase, with an I50app of 18.3 μM.
References
[1] Franck E Dayan. “Sarmentine, a natural herbicide from Piper species with multiple herbicide mechanisms of action.” Frontiers in Plant Science (2015): 222.
SarMentine Preparation Products And Raw materials
Raw materials
Preparation Products
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