Spermidine
SperMidin · N1-(3-AMINOPROPYL)BUTANE-1,4-DIAMINE · Spermidine-Rich Wheat Germ Extract · Spermidine,99% · SPERMIDINE FREE BASE · 1,4-Butanediamine, N-(3-aminopropyl)- · 3.2 Kg · Spermidie
Identifiers & Physical Properties
| CAS No. | 124-20-9 |
|---|---|
| Molecular formula | C7H19N3 |
| Average molar mass | 145.25 g/mol |
| Monoisotopic mass | 145.15789761 g/mol |
| SMILES | NCCCCNCCCN |
| InChIKey | ATHGHQPFGPMSJY-UHFFFAOYSA-N |
| PubChem CID | 1102 |
| ChEMBL | CHEMBL19612 |
| ChEBI | CHEBI:16610 |
| EC No. | 204-689-0 |
| DTXSID | DTXSID4036645 |
Chemical & Physical Properties
| XLogP | -1 |
|---|---|
| Topological polar surface area | 64.1 |
| Hydrogen bond donors | 3 |
| Hydrogen bond acceptors | 3 |
| Rotatable bonds | 7 |
| Heavy atoms | 10 |
| Formal charge | 0 |
| Complexity | 56.8 |
| Drugs | Pharmaceuticals -> Listed in ZINC15 |
| Fragrances | Fragrance Ingredient (1,4-Butanediamine, N-(3-aminopropyl)-) -> IFRA transparency List |
| Melting point | < 25 °C23-25 °C |
| Physical Description | Solid |
| Collision Cross Section | 136.5 Ų [M+Na]+ [CCS Type: DTMethod: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]131.9 Ų [M+H]+ [CCS Type: DTMethod: single field calibrated with Agilent tune mix (Agilent)]136.2 Ų [M+Na]+ |
| Boiling point | 128-130 °C (14 mmHg) |
| Density | 1.00 g/mL at 20 °C |
| Refractive index | n20/D 1.479(lit.) |
| Flash point | >230 °F |
| Storage conditions | room temp |
| Solubility | H2O: 1 M at 20 °C, clear, colorlessMiscible with water, ethanol and ether. |
| Physical state | Liquid After Melting |
| pKa (acidity coefficient) | 10.53±0.19(Predicted) |
| Color | Clear colorless |
| Specific gravity | 0.925 |
| pH | 12.0-13.5 (25℃, 1M in H2O) |
| Odor | Ichtyal, ammoniacal |
| Biological source | synthetic |
| λmax | λ: 260 nm Amax: 0.1λ: 280 nm Amax: 0.05 |
| Sensitivity | Air Sensitive |
| Merck | 14,8742 |
| BRN | 1698591 |
| Stability | Stable, but air-sensitive and very hygroscopic - store under argon. Incompatible with acids, acid chlorides, acid anhydrides, oxidizing agents. |
| Cosmetics Ingredients Functions | ANTIOXIDANTHAIR CONDITIONING |
| InChI | 1S/C7H19N3/c8-4-1-2-6-10-7-3-5-9/h10H,1-9H2 |
| InChIKey | ATHGHQPFGPMSJY-UHFFFAOYSA-N |
| SMILES | NCCCCNCCCN |
| CAS DataBase Reference | 124-20-9(CAS DataBase Reference) |
| EWG's Food Scores | 1 |
| FDA UNII | U87FK77H25 |
| EPA Substance Registry System | 1,4-Butanediamine, N-(3-aminopropyl)- (124-20-9) |
| UNSPSC Code | 85151701 |
| NACRES | NA.52 |
| GHS pictogram | GHS05 |
| Signal word | Danger |
| GHS hazard statements | H314 |
| GHS precautionary statements | P280-P303+P361+P353-P304+P340+P310-P305+P351+P338-P363-P405 |
| Personal protective equipment (PPE) | Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter |
| Hazard symbols | C |
| Risk statements (R) | 34 |
| Safety statements (S) | 26-36/37/39-45-27 |
| UN transport number | UN 2735 8/PG 2 |
| Water hazard class (WGK) | 3 |
| RTECS number | EJ7000000 |
| F | 3-10-34 |
| TSCA inventory status | TSCA listed |
| Hazard class | 8Eye Dam. 1Skin Corr. 1B |
| Packing group | III |
| Customs code | 29212900 |
| Storage class | 8A - Combustible corrosive hazardous materials |
Safety & Regulations
| GHS classification | DangerH314 (100%): Causes severe skin burns and eye damage [Danger Skin corrosion/irritation]P260, P264, P264+P265, P280, P301+P330+P331, P302+P361+P354, P304+P340, P305+P354+P338, P316, P317, P321, P363, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 83 reports by companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Regulatory information | Spermidine: Does not have an individual approval but may be used under an appropriate group standard |
| Hazard Classes and Categories | Skin Corr. 1A (100%) |
| Treatment | Kidney dialysis is usually needed to relieve the symptoms of uremic syndrome until normal kidney function can be restored. |
| Health effects | Chronic exposure to uremic toxins can lead to a number of conditions including renal damage, chronic kidney disease and cardiovascular disease. |
| Exposure routes | Endogenous, Ingestion, Dermal (contact) |
| Toxicity summary | Uremic toxins such as spermidine are actively transported into the kidneys via organic ion transporters (especially OAT3). Increased levels of uremic toxins can stimulate the production of reactive oxygen species. This seems to be mediated by the direct binding or inhibition by uremic toxins of the enzyme NADPH oxidase (especially NOX4 which is abundant in the kidneys and heart) (A7868). Reactive oxygen species can induce several different DNA methyltransferases (DNMTs) which are involved in the silencing of a protein known as KLOTHO. KLOTHO has been identified as having important roles in anti-aging, mineral metabolism, and vitamin D metabolism. A number of studies have indicated that KLOTHO mRNA and protein levels are reduced during acute or chronic kidney diseases in response to high local levels of reactive oxygen species (A7869). |
| Signs and Symptoms | As a uremic toxin, this compound can cause uremic syndrome. Uremic syndrome may affect any part of the body and can cause nausea, vomiting, loss of appetite, and weight loss. It can also cause changes in mental status, such as confusion, reduced awareness, agitation, psychosis, seizures, and coma. Abnormal bleeding, such as bleeding spontaneously or profusely from a very minor injury can also occur. Heart problems, such as an irregular heartbeat, inflammation in the sac that surrounds the heart (pericarditis), and increased pressure on the heart can be seen in patients with uremic syndrome. Shortness of breath from fluid buildup in the space between the lungs and the chest wall (pleural effusion) can also be present. |
Applications & Uses
Description
Spermidine is an endogenous polyamine. It is formed from putrescine by spermidine synthase.
Uses
Spermidine can be used in electroporation while transferring the DNA into the cell under the electrical impulse. May be used for purification of DNA-binding proteins. Spermidine is also used, along with calcium chloride, for precipitating DNA onto microprojectiles for bombardment with a gene gun.
Preparation & Synthesis
Preparation
The linker resin 2 was used in the synthesis of spermidine. In order to initiate the preparation the 2-nitrossulfonamide was anchored on the resin 2 by reaction in THF under reflux. The resulting resin 3 then reacted with 4-bromobutylphthalimide in acetonitrile in the presence of Cs2CO3 as base, generating the resin 4. Protected spermidine 5 was cleaved from resin 4 after treatment with hydrate hydrazine at room temperature. Spermidine 5 was previously prepared by our group in solution system utilizing Fukuyama's sulfonamide.Synthesis and Characterization of a Linker for Primary Amines used in the Solid Phase Organic Synthesis of SpermidineJ. Braz. Chem. Soc., Vol. 22, No. 1, 86-91, 2011DOI: 10.1590/S0103-50532011000100011