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Spermine

Spermine structure

CAS No:
71-44-3
Formula:
C10H26N4
Chemical Name:
Spermine
Synonyms:
1,4-Butanediamine,N1,N4-bis(3-aminopropyl)-;Spermine;1,4-Butanediamine,N,N′-bis(3-aminopropyl)-;N1,N4-Bis(3-aminopropyl)-1,4-butanediamine;Gerontine;Musculamine;Neuridine;4,9-Diazadodecane-1,12-diamine;Spermin;N,N′-Bis(3-aminopropyl)-1,4-tetramethylenediamine;1,5,10,14-Tetraazatetradecane;N,N′-Bis(3-aminopropyl)-1,4-butanediamine;NSC 268508;N,N′-Bis(3-aminopropyl)butanediamine;N,N′-Bis(3-Aminopropyl)-1,4-diaminobutane;115-04-8;1127437-73-3
Categories:
Cosmetic Ingredient > Skin Conditioning

Description

Spermine functions directly as a free radical scabenger to protect DNA from free radical attack.

Liquid|Solid

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 polyazaalkane and a tetramine. It is a conjugate base of a spermine(4+).|Spermine is a spermidine-derived biogenic polyamine found as a polycation at all pH values. Found in various tissues and organisms, it often acts as an essential growth factor in some bacterial species. Spermine is associated with nucleic acids, particularly in viruses, and is thought to stabilize the helical structure.|Spermine is a polyamine that has a similar structure to tetradecane but the carbons at positions 1, 5, 10 and 14 are replaced by nitrogens. Spermine plays a broad role in cellular metabolic processes.|A biogenic polyamine formed from spermidine. It is found in a wide variety of organisms and tissues and is an essential growth factor in some bacteria. It is found as a polycation at all pH values. Spermine is associated with nucleic acids, particularly in viruses, and is thought to stabilize the helical structure.

Spermine Basic Attributes

Molecular Weight：

202.34

Exact Mass：

202.34

BRN：

1751791

EC Number：

206-189-8

UNII：

2FZ7Y3VOQX

NSC Number：

268508

DSSTox ID：

DTXSID7028936|DTXSID9058781

NCI Thesaurus Code：

C106406

HScode：

2921290000

Characteristics

PSA：

76.1

XLogP3：

-1.1

Appearance：

powder

Density：

0.9±0.1 g/cm3

Melting Point：

29 °C

Boiling Point：

172-176 °C @ Press: 40 Torr

Flash Point：

>230 °F

Refractive Index：

1.485

Water Solubility：

soluble in chloroform, methanol, water and lower alcohols. Insoluble in ether, benzene and petroleum ether.

Storage Conditions：

2-8°C

Collision Cross Section：

148.2 Å² [M+H]+ [CCS Type: DT, Method: single field calibrated with Agilent tune mix (Agilent)]|148.6 Å² [M+H]+ [CCS Type: DT, Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]|151.5 Å² [M+Na]+ [CCS Type: DT, Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]|148.6 Å² [M+H]+

Safety Information

Packing level：

Ⅱ

Hazard category：

Transport codes：

UN 3259 8/PG 2

wgk germany：

hazard class code：

36/38-34

safety instructions：

26-36-45-36/37/39-27

RTECS Number：

EJ7230000

Marks：

Xi,C

Precautionary statement(s)：

P280-P305 + P351 + P338-P310

Hazard Statements：

H314

GHS Classification：

|Danger|H226 (99.88%): Flammable liquid and vapor [Warning Flammable liquids]|P210, P233, P240, P241, P242, P243, P261, P264, P272, P273, P280, P301+P310, P302+P352, P303+P361+P353, P305+P351+P338, P321, P331, P332+P313, P333+P313, P337+P313, P362, P363, P370+P378, P391, P403+P235, P405, and P501|Aggregated GHS information provided by 1759 companies from 17 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|H314 (100%): Causes severe skin burns and eye damage [Danger Skin corrosion/irritation]|P260, P264, P280, P301+P330+P331, P303+P361+P353, P304+P340, P305+P351+P338, P310, P321, P363, P405, and P501|Aggregated GHS information provided by 135 companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|Warning|H316: Causes mild skin irritation [Warning Skin corrosion/irritation]|P261, P264, P272, P280, P302+P352, P305+P351+P338, P321, P332+P313, P333+P313, P337+P313, P363, and P501

Drug Information

Drug Indication：

For nutritional supplementation, also for treating dietary shortage or imbalance

Pharmacology：

Spermine is a polyamine. It is an organic molecule that is involved in cellular metabolism.

Mechanism of Action：

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.

MeSH Entry Terms：

Spermine

Spermine Use and Manufacturing

Methods of Manufacturing

Fatty alcohols made from coconut oil are made by sulfuric acid sulfonation.

Uses

Biogenic polyamine formed from spermidine and occurring in almost all tissues. Essential for both normal and neoplastic tissue growth. Involved in the modulation of calcium-dependent immune processes

Adhesives and sealant chemicals

Cleaning and furnishing care products

Production

10,000,000 - 50,000,000 lb

Manufacturing Info：

Adhesive manufacturing|Hydrocarbons, terpene processing by-products: ACTIVE|1,4-Butanediamine, N1,N4-bis(3-aminopropyl)-: ACTIVE

Computed Properties

Molecular Weight:202.34
XLogP3:-1.1
Hydrogen Bond Donor Count:4
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:11
Exact Mass:202.21574685
Monoisotopic Mass:202.21574685
Topological Polar Surface Area:76.1
Heavy Atom Count:14
Complexity:86.1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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