Kohlenwasserstoffe, Nebenprodukte bei der Verarbeitung von Terpen

Spermine

HCID 1103CAS 68956-56-9

Grundinformationen

Standard-SMILES
NCCCNCCCCNCCCN
InChIKey
PFNFFQXMRSDOHW-UHFFFAOYSA-N
Summenformel
C10H26N4
Durchschnittliche Molmasse
202,34 g/mol
Monoisotopische Masse
202,21574683

Überblick

Spermine is a polyazaalkane that is tetradecane in which the carbons at positions 1, 5, 10 and 14 are replaced by nitrogens. Spermine has broad actions on cellular metabolism. It has a role as an antioxidant, an immunosuppressive agent and a fundamental metabolite. It is a tetramine and a polyazaalkane. It is a conjugate base of a spermine(4+).

Namen und Bezeichner

Bevorzugter Name
Spermine
IUPAC
N,N'-bis(3-aminopropyl)butane-1,4-diamine
Lokaler Name
Kohlenwasserstoffe, Nebenprodukte bei der Verarbeitung von Terpen
Englischer Name
Dipentene
Summenformel
C10H16
Molmasse
136.24

Namen und Synonyme

spermine71-44-3musculamineneuridinegerontineSperminN,N'-Bis(3-aminopropyl)-1,4-butanediamineDiaminopropyltetramethylenediamine4,9-Diaza-1,12-dodecanediamineN,N'-Bis(3-aminopropyl)butane-1,4-diamineSpermine, puriss1,4-Bis(aminopropyl)butanediamine
Weitere Namen anzeigen
DipenteneDIPENTENE-CDipentene NOGLIDSOL(R) 175GLIDSOL(R) 140THYME TERPENESGLIDSOL(R) 66-2GLIDSOL(R) 5140RHODINYL TERPENESLIME OIL TERPENES
1,4-Butanediamine, N,N'-bis(3-aminopropyl)-4,9-DiazadodecamethylenediamineGerotineSpermina4,9-Diazadodecane-1,12-diamine2FZ7Y3VOQXActilip sp-911,5,10,14-Tetraazatetradecane

Datenbank-Bezeichner

CAS
68956-56-9、71-44-3
PubChem CID
1103
DTXSID
DTXSID9058781
ChEMBL
CHEMBL23194
ChEBI
CHEBI:15746
UNII
2FZ7Y3VOQX
EC Number
200-754-2
Nikkaji
J5.246I

Eigenschaften

Berechnete Struktureigenschaften

XLogP
-1,1
Polarare Oberfläche (TPSA)
76,1 Ų
H-Brücken-Donoren
4
H-Brücken-Akzeptoren
4
Frei drehbare Bindungen
11
Schwere Atome
14

Experimentelle und physikochemische Eigenschaften

Chemical ClassesBiological Agents -> Amino Acids and Derivatives
DrugsPharmaceuticals -> Listed in ZINC15
Solubility> 100 mg/mL
Boiling Point150-150 °C
Melting Point29 °C
Physical Description · 2 Einträge

Solid; Absorbs carbon dioxide from air; [Merck Index] Colorless solidified mass or fragments; mp = 28-30 deg C; [Sigma-Aldrich MSDS]

Solid

Physikochemische Eigenschaften

Siedepunkt
173 · 173-190°C
Dichte
0.85 · 0.850
Dampfdruck
6.9 hPa · 6.9hPa at 20℃
Brechungsindex
20 · n20/D 1.469
Flammpunkt
42 °C · 42°C
storage temp.
Flammables area

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 4 Einträge

Danger

H314 (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 76 reports by companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Gefahrenhinweise

Regulatory Information4,9-Diazadodecamethylenediamine: Does not have an individual approval but may be used under an appropriate group standard
Hazards Summary · 1 Eintrag

Corrosive; [Merck Index] Oral LD30 (mouse) = 650 mg/kg; Causes lung changes, renal tubular changes, and dehydration in intraperitoneal lethal-dose studies of rats; Causes somnolence and convulsions in oral and subcutaneous lethal-dose studies of mice; Causes hypoglycemia and effects on enzymes and lipids in repeated-dose oral studies of rats; [RTECS] Causes burns; Inhalation may cause corrosive injuries to upper respiratory tract; [Sigma-Aldrich MSDS]

Hazard Classes and CategoriesSkin Corr. 1C (100%)

Toxikologische Informationen

TreatmentKidney dialysis is usually needed to relieve the symptoms of uremic syndrome until normal kidney function can be restored.
Health EffectsChronic exposure to uremic toxins can lead to a number of conditions including renal damage, chronic kidney disease and cardiovascular disease.
Adverse EffectsDermatotoxin - Skin burns.
Exposure RoutesEndogenous, Ingestion, Dermal (contact)
Toxicity Summary · 1 Eintrag

Uremic toxins such as spermine 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). Spermine is derived from spermidine by spermine synthase. Spermine is a polyamine, a small organic cations that is absolutely required for eukaryotic cell growth. Spermine, is normally found in millimolar concentrations in the nucleus. Spermine functions directly as a free radical scavenger, and forms a variety of adducts that prevent oxidative damage to DNA. Oxidative damage to DNA by reactive oxygen species is a continual problem that cells must guard against to survive. Hence, spermine is a major natural intracellular compound capable of protecting DNA from free radical attack. Spermine is also implicated in the regulation of gene expression, the stabilization of chromatin, and the prevention of endonuclease-mediated DNA fragmentation.

Signs and Symptoms · 1 Eintrag

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.

Sicherheitsdaten

wgk
3
tsca
TSCA listed
ridadr
UN 2052
hs_code
29021900
risk_code
10-38-43-50/53-65
Toxizität
The acute oral LD50 value in rats was reported as 5.3 g/kg (4.6-6.0 g/kg) (Moreno, 1972a). The acute dermal LD50 value for d-limonene was reported as > 5 g/kg (Moreno, 1972b).

Chemie und Industrie

Pharmakologische Informationen

PharmacodynamicsSpermine is a polyamine. It is an organic molecule that is involved in cellular metabolism.
Mechanism of Action · 1 Eintrag

Spermine is derived from spermidine by spermine synthase. Spermine is a polyamine, a small organic cations that is absolutely required for eukaryotic cell growth. Spermine, is normally found in millimolar concentrations in the nucleus. Spermine functions directly as a free radical scavenger, and forms a variety of adducts that prevent oxidative damage to DNA. Oxidative damage to DNA by reactive oxygen species is a continual problem that cells must guard against to survive. Hence, spermine is a major natural intracellular compound capable of protecting DNA from free radical attack. Spermine is also implicated in the regulation of gene expression, the stabilization of chromatin, and the prevention of endonuclease-mediated DNA fragmentation.

Metabolism/MetabolitesUremic toxins tend to accumulate in the blood either through dietary excess or through poor filtration by the kidneys. Most uremic toxins are metabolic waste products and are normally excreted in the urine or feces.
Tissue LocationsBrain
Cellular LocationsCytoplasm
Metabolite PathwaysSpermidine and Spermine Biosynthesis

Verwendung und Herstellung

Uses · 2 Einträge

Used as a tool in biochemical research; [Merck Index]

For nutritional supplementation, also for treating dietary shortage or imbalance

General Manufacturing Information1,4-Butanediamine, N1,N4-bis(3-aminopropyl)-: ACTIVE
Anwendungen · 2 Einträge

OccurrenceFound in a very large number of oils, including oils of lemongrass, citronella, palmarosa, cardamon and bergamot, Siberian pine needle oil and several other essential oils including turpentine oils of various origin (Guenther, 1949).

VerwendenDipentene (Limonene) is a monoterpene olefin having potential applications in polymer and fuel chemistry. It is also widely used as flavoring and fragrance agent. Dipentene (limonene) is a promising green solvent. Kinetics of the reactions of limonene with OH and OD radicals has been investigated in a low pressure flow tube reactor coupled with a quadrupole mass spectrometer.

Darstellung · 1 Eintrag

synthetischeDipentene is a by-product in the manufacture of terpineol and in various synthetic products made from α-pinene or turpentine oil (Arctander, 1969). Dipentene is mainly composed of terpene hydrocarbons. because of its refreshing pine, lime aroma and low cost, dipentene is mainly used as cost effective ingredient for household products.

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