Dihydrolysergic acid
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Dihydrolysergic acid is a fungal ergot alkaloid and also the dihydro analog of lysergic acid. Dihydrolysergic acid serves as a precursor for vasodilatory ergot alkaloid-derived drugs. Dihydrolysergic acid can be biosynthesized by expressing intron-free synthetic Claviceps africana cloA in an Neosartorya fumigata easM knockout strain.
For research use only. We do not sell to patients.
- Purity: 99.89%
- CAS No.: 5878-43-3
- Formula: C16H18N2O2
- Molecular Weight:270.33
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Storage:Powder -20°C, 3 years ; In solvent -80°C, 6 months , -20°C, 1 month
All Endogenous Metabolite Isoforms
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Biological Activity
Dihydrolysergic acid (compound 1) is prepared via alkaline catalytic hydrolysis of Methyl (6aR,9R,10aR)-7-Methyl-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline-9-carboxylate (compound 18)[1].
Dihydrolysergic acid (DHLA) is biosynthesized when intron-free synthetic Claviceps africana cloA is expressed in festuclavine-accumulating Neosartorya fumigata easM knockout strains[2].
MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.
Chemical Information
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CAS No. 5878-43-3
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Appearance Solid
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Molecular Weight 270.33
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Formula C16H18N2O2
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Color White to off-white
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SMILES
CN1[C@@]2([H])[C@@](C[C@H](C1)C(O)=O)([H])C3=CC=CC4=C3C(C2)=CN4
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Structure Classification
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Initial Source
Claviceps gigantea
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Shipping
Room temperature in continental US; may vary elsewhere.
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Storage
Powder -20°C 3 years In solvent -80°C 6 months -20°C 1 month
Solvent & Solubility
DMSO : 2 mg/mL (7.40 mM; ultrasonic and warming and heat to 60°C; Hygroscopic DMSO has a significant impact on the solubility of product, please use newly opened DMSO)
Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 6 months; -20°C, 1 month. When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.
Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 6 months; -20°C, 1 month. When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.
Concentration (start) × Volume (start) = Concentration (final) × Volume (final)
Purity & Documentation
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Data Sheet (272 KB)
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SDS (393 KB)
- English - EN (393 KB)
- Français - FR (393 KB)
- Deutsch - DE (393 KB)
- Norwegian - NO (393 KB)
- Español - ES (393 KB)
- Swedish - SV (393 KB)
- Italian - IT (393 KB)
- Korean - KR (393 KB)
- Portuguese - PT (393 KB)
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Handling Instructions (2659 KB)
References
[1]. Lee K, et al. Total synthesis of dihydrolysergic acid and dihydrolysergol: development of a divergent synthetic strategy applicable to rapid assembly of D-ring analogs. Tetrahedron. 2015 Sep 02;71(35):5897-5905. [Content Brief]
[2]. Arnold SL, et al. Biosynthesis of the Pharmaceutically Important Fungal Ergot Alkaloid Dihydrolysergic Acid Requires a Specialized Allele of . Applied and environmental microbiology. 2017 Jul 15;83(14):e00805-17. [Content Brief]
Complete Stock Solution Preparation Table
Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 6 months; -20°C, 1 month. When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.
| Optional Solvent | Concentration Solvent Mass | 1 mg | 5 mg | 10 mg | 25 mg |
|---|---|---|---|---|---|
| DMSO | 1 mM | 3.6992 mL | 18.4959 mL | 36.9918 mL | 92.4796 mL |
| 5 mM | 0.7398 mL | 3.6992 mL | 7.3984 mL | 18.4959 mL |