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Home > Encyclopedia > Nonaethylene glycol monododecyl ether

Nonaethylene glycol monododecyl ether

pharmaceutical raw materials
Nonaethylene glycol monododecyl ether structure

Nonaethylene glycol monododecyl ether 

structure
  • CAS No:

    3055-99-0

  • Formula:

    C30H62O10

  • Chemical Name:

    Nonaethylene glycol monododecyl ether

  • Synonyms:

    3,6,9,12,15,18,21,24,27-Nonaoxanonatriacontan-1-ol;Do 9/R3;Ethanol,2-[2-[2-[2-[2-[2-[2-[2-[2-(dodecyloxy)ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]-;Nonaethylene glycol monododecyl ether;C12E9;Nonaoxyethylene monododecyl ether;C12EO9;2-[2-[2-[2-[2-[2-[2-[2-(2-Dodecoxyethoxy)ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethanol;95297-49-7;73579-17-6

  • Categories:

    Cosmetic Ingredient  >  Emulsifying Agent

Description

Nonaethylene glycol monododecyl ether (Nonaoxyethylene monododecyl ether) is a nonionic surfactant and polyethylene glycol (PEG) detergent that can be used to form initial coalesced O/W emulsion droplets, as well as for protein separation and purification[1][2][3].


Polidocanol is a hydroxypolyether that is nonaethylene glycol in which one of the terminal hydroxy functions is substituted by a lauryl (dodecyl) group. It has a role as a nonionic surfactant, a hepatotoxic agent and a sclerotherapy agent. It derives from a nonaethylene glycol.|Polidocanol is a sclerosing agent indicated to treat uncomplicated spider veins (varicose veins ≤1 mm in diameter) and uncomplicated reticular veins (varicose veins 1 to 3 mm in diameter) in the lower extremity. It is marketed under the brand names Asclera and Varithena. The formula for Polidocanol has the structural formula C12H25(OCH2CH2)nOH, a mean extent of polymerization (n) of approximately 9 and a mean molecular weight of approximately 600.

Nonaethylene glycol monododecyl ether Basic Attributes

582.807

582.81

500-027-2

DTXSID5039721

COLORLESS TO YELLOW LIQUID

C05BB02|C - Cardiovascular system

2909499000

Characteristics

103.30000

2.18

1.0±0.1 g/cm3

33.3-33.6 °C

615.9±50.0 °C at 760 mmHg

326.3±30.1 °C

1.459

miscible

2-8ºC

7.5X10-11 mm Hg at 25 °C (est)

PLEASANT

Henry's Law constant = 6.8X10-18 atm-cu m/mol at 25 °C (est)

Contains an average of nine ethylene oxide units and has an average molecular weight of about 600|LINEAR MOL CONSISTING OF A DODECYL ALCOHOL ATTACHED BY A STABLE ETHER LINKAGE TO A POLYETHYLENE GLYCOL MOIETY|OILY

-6200 CAL/G

Safety Information

NONH for all modes of transport

3

23-24/25

P261, P264, P270, P271, P273, P280, P301+P312, P302+P352, P304+P340, P305+P351+P338, P310, P312, P321, P330, P332+P313, P337+P313, P362, P391, P403+P233, P405, P501

H302

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal and plant life; and conformance with environmental and public health regulations.

|Danger|H302 (79.87%): Harmful if swallowed [Warning Acute toxicity, oral]|P264, P270, P273, P280, P301+P312, P302+P352, P305+P351+P338, P310, P321, P330, P332+P313, P337+P313, P362, and P501|Aggregated GHS information provided by 1690 companies from 30 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|H302 (44.44%): Harmful if swallowed [Warning Acute toxicity, oral]|P261, P264, P270, P271, P273, P280, P301+P312, P302+P352, P304+P340, P305+P351+P338, P310, P312, P321, P330, P332+P313, P337+P313, P362, P391, P403+P233, P405, and P501|Aggregated GHS information provided by 9 companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Equipment: plastic gloves, goggles.

DRY CHEMICAL, CARBON DIOXIDE, OR ALCOHOL FOAM.

CONTACT WITH SKIN MAY CAUSE IRRITATION.

| 0 - Materials that, under emergency conditions, would offer no hazard beyond that of ordinary combustible materials.| 1 - Materials that must be preheated before ignition can occur. Materials require considerable preheating, under all ambient temperature conditions, before ignition and combustion can occur.| 0 - Materials that in themselves are normally stable, even under fire conditions.

Toxicity

Most adverse reactions are related to the intravenous administration such as local irritation, pain, and hematoma. Extravasation can also be an issue.

When the smooth musculature of isolated spirally opened up portal veins of rats was subjected to polidocanol, the injury produced was to some extent reversible. O-(beta-hydroxyethyl)rutoside prevented the injurious effect if applied before polidocanol. It also displayed a curative effect against the polidocanol-induced injury.

LD50 Guinea pig Intravenous 38 mg/kg|LD50 Guinea Pig oral 384 mg/kg|LD50 Mouse Intravenous 100 mg/kg|LD50 Mouse oral 1170 mg/kg|For more Non-Human Toxicity Values (Complete) data for DODECYL ALCOHOL, ETHOXYLATED (8 total), please visit the HSDB record page.

Plasma protein binding was not measured.

Dodecyl alcohol, ethoxylated's production and use as a solvent, nonionic emulsifier, and pharmaceutical aid(1) may result in its release to the environment through various waste streams(SRC).

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 150(SRC), determined from a structure estimation method(2), indicates that dodecyl alcohol, ethoxylated is expected to have high mobility in soil(SRC). Volatilization of dodecyl alcohol, ethoxylated from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 6.9X10-18 atm-cu m/mole(SRC), using a fragment constant estimation method(3). Dodecyl alcohol, ethoxylated is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 7.5X10-11 mm Hg at 25 °C(SRC), determined from a fragment constant method(4). Utilizing the Japanese MITI test, 74% of the Theoretical BOD was reached in 4 weeks(5) indicating that biodegradation is an important environmental fate process in soil(SRC).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 150(SRC), determined from a structure estimation method(2), indicates that dodecyl alcohol, ethoxylated is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 6.9X10-18 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). According to a classification scheme(5), an estimated BCF of 81(SRC), from an estimated log Kow of 3.40(6) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is moderate. Utilizing the Japanese MITI test, 74% of the Theoretical BOD was reached in 4 weeks(8) indicating that biodegradation is an important environmental fate process in water(SRC).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), dodecyl alcohol, ethoxylated, which has an estimated vapor pressure of 7.5X10-11 mm Hg at 25 °C((SRC), determined from a fragment constant method(2), is expected to exist solely in the particulate phase in the ambient atmosphere. Particulate-phase dodecyl alcohol, ethoxylated may be removed from the air by wet and dry deposition(SRC). Dodecyl alcohol, ethoxylated does not contain chromophores that absorb at wavelengths >290 nm(3) and, therefore, is not expected to be susceptible to direct photolysis by sunlight(SRC).

Dodecyl alcohol, ethoxylated is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(1). Dodecyl alcohol, ethoxylated does not contain chromophores that absorb at wavelengths >290 nm(1) and, therefore, is not expected to be susceptible to direct photolysis by sunlight(SRC).

An estimated BCF of 81 was calculated in fish for dodecyl alcohol, ethoxylated(SRC), using an estimated log Kow of 3.40(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is moderate(SRC).|To study the relationship between the exposure concentration of surfactants and their concentration factors in fish bodies, carp were exposed to several concentration of 3 surfactants, including (14)C-labeled dodecyl octa(oxyethylene) ether ((14)C-C12-AE(8)). Although the concentration in fish of the (14)C-radioactivity derived from the (14)C-C12-AE(8) reached their equilibrium after 72 hr of exposure, their concentration factors differed according to the concentration of the surfactant in each solution. They ranged from 39 at 9.9 mug/L to 220 at 1000 mug/L.

Using a structure estimation method based on molecular connectivity indices(1), the Koc of dodecyl alcohol, ethoxylated can be estimated to be 150(SRC). According to a classification scheme(2), this estimated Koc value suggests that dodecyl alcohol, ethoxylated is expected to have high mobility in soil. Dodecyl alcohol, ethoxylated has a reported Freundlich isotherm coefficient (log K) of 7.79, using a subhumid grassland Morton soil from western North Dakota with a fractional organic content of 0.0096(3).

The Henry's Law constant for dodecyl alcohol, ethoxylated is estimated as 6.9X10-18 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that dodecyl alcohol, ethoxylated /is expected to be essentially nonvolatile from water surfaces(2). Dodecyl alcohol, ethoxylated's Henry's Law constant indicates that volatilization from moist soil surfaces will not occur(SRC). Dodecyl alcohol, ethoxylated is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 7.5X10-11 mm Hg(SRC), determined from a fragment constant method(3).

NIOSH (NOES Survey 1981-1983) has statistically estimated that 104,035 workers (60,645 of these were female) were potentially exposed to dodecyl alcohol, ethoxylated in the US(1). Occupational exposure to dodecyl alcohol, ethoxylated may occur through inhalation and dermal contact with this compound at workplaces where dodecyl alcohol, ethoxylated is produced or used. Use data indicate that the general population may be exposed to dodecyl alcohol, ethoxylated via dermal contact with consumer products and medications containing dodecyl alcohol, ethoxylated(SRC).

Drug Information

Polidocanol is a sclerosing agent indicated to treat uncomplicated spider veins and uncomplicated reticular veins in the lower extremity.|FDA Label

A randomized, open, multicenter study comparing the safety and efficacy of single or repeated endoscopic injection of Beriplast, a fibrin glue, with those of single endoscopic injection of 1% polidocanol (Aethoxysklerol) for the prevention of GI hemorrhage was conducted in 850 patients (ages 21-94 yr) with bleeding gastroduodenal ulcers. Recurrent bleeding rates among patients in whom the rates could be assessed were 58 of 254 in the polidocanol group, 51 of 266 in the fibrin glue single group, and 41 of 270 in the fibrin glue repeated group. The difference between fibrin glue repeated treatment and polidocanol was significant. Treatment failed, making other therapy necessary, in 34 of 261 in the polidocanol group, 34 of 274 in the fibrin glue single group, and 21 of 274 in the fibrin glue repeated group. The 30 day mortality rates were low in all groups. The safety profiles of the 3 treatments were similar.|Sclerosing Solutions; Tissue Adhesives; Detergents|IN VARIOUS CONCN THESIT AND A MIXT OF SIMILAR ALKYL ETHOXYLATES KNOWN BY THE CODE NAME SCH 600 HAVE BEEN USED IN MAN AND ANIMALS FOR CORNEAL ANESTHESIA, FOR MUCOSAL ANESTHESIA PRECEDING ENDOSCOPY, FOR RELIEF FROM ITCHING (APPLIED LOCALLY TO THE ANUS, RECTUM, VAGINA, SKIN LESIONS, ETC), FOR NERVE BLOCKS (BY INFILTRATION), FOR SPERMICIDAL ACTIVITY (WHEN INSTILLED IN THE VAGINA), FOR RELIEF OF PAIN FROM PEPTIC ULCER (WHEN INGESTED).|MEDICATION (VET): PERFUSION OF ISOLATED GUINEA PIG HEARTS WITH POLIDOCANOL @ 20, 40, OR 100 UG DOSE-DEPENDENTLY DECR HEART RATE & CONTRACTILE STRENGTH & INCR ATRIAL REFRACTORY PERIOD. IN RATS, POLIDOCANOL INFUSION @ 10, 20, 30, AND 40 MG/KG DECR BLOOD PRESSURE & HEART RATE. DURING INFUSION, PQ INTERVAL OF THE ECG WAS ALSO PROLONGED. THESE CHANGES WERE DISCUSSED IN TERMS OF ITS USE FOR SCLEROTHERAPY OF PATIENTS WITH ESOPHAGEAL VARICES.|For more Therapeutic Uses (Complete) data for DODECYL ALCOHOL, ETHOXYLATED (6 total), please visit the HSDB record page.

3. 3= MODERATELY TOXIC: PROBABLE ORAL LETHAL DOSE (HUMAN) 0.5-5 G/KG, BETWEEN 1 OZ AND 1 PT (OR 1 LB) FOR 70 KG PERSON (150 LB).

Polidocanol has a concentration and volume dependent damaging effect on the blood vessel endothelium.

When given intravenously, the maximum blood concentrations were reached in 15 mins.|Route of elimination was not indicated.|When given intravenously, the volume of distribution was 35-82L.|Sytemic clearance was 0.2-0.4 L/min.

Metabolism was not measured.

The half-life is approximately 1.5 h.

When administered, polidocanol locally damages blood vessel endothelium. Following the endothelial damage, platelets aggregate at the site and attach to the venous wall eventually resulting in a dense network of platelets, cellular debris, and fibrin that occludes the vessel. Eventually the vessel is replaced by connective fibrous tissue.

/SRP:/ Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR if necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on the left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Poisons A and B/|/SRP:/ Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if needed. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 mL/kg up to 200 mL of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool ... . Cover skin burns with dry sterile dressings after decontamination ... . /Poisons A and B/|/SRP:/ Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Positive-pressure ventilation techniques with a bag valve mask device may be beneficial. Consider drug therapy for pulmonary edema ... . Consider administering a beta agonist such as albuterol for severe bronchospasm ... . Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start IV administration of D5W /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam or lorazepam ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poisons A and B/

/HUMAN EXPOSURE STUDIES/ THE TOXICITY OF POLYOXYETHYLENE LAURYL ETHER TO THE SKIN WAS DETERMINED BY THE CLOSED PATCH TEST. IT WAS HARMFUL TO THE BLOOD VESSEL OF THE DERMAL LAYER BUT HAD LITTLE EFFECT ON THE EPIDERMAL LAYER.|/ALTERNATIVE and IN VITRO TESTS/ To investigate the lytic effects of sodium tetradecyl sulphate (STS) and polidocanol (POL) on erythrocytes, platelets, endothelial cells and platelet-derived microparticle (PDMP) formation in vitro and the potential protective effects of serum albumin and agents such as procaine. The effects of sclerosants were studied in blood samples obtained from normal individuals. Absorbance densitometry was used to assess the lytic effects of sclerosants on blood cells and cultured human microvascular endothelial cells (HMEC) in plasma and in saline. PDMP were quantified by flow cytometry. Hemolysis occurred in whole blood at sclerosant concentrations greater than 0.25% for STS and above 0.45% for POL. Similar concentrations of both agents caused platelet and endothelial cell lysis. Both sclerosants released PDMP at low concentrations but destroyed PDMP at higher concentrations. Albumin significantly reduced the lytic effect of both sclerosants on all cells but had a greater inhibitory effect on POL. Protamine at 0.01% had a neutralizing effect on STS, whereas procaine and lignocaine showed no such activity. Sclerosants at therapeutic concentrations lyse blood cells and endothelial cells in vitro. This effect is strongly reduced by serum albumin possibly contributing towards the low incidence of thromboembolic complications of sclerotherapy.|/OTHER TOXICITY INFORMATION/ The aim of our case series was to show the therapeutic effect and the safety of the use of polidocanol foam in ultrasound-guided sclerotherapy treatment of relatively small postoperative seromas after varicose vein surgery. We treated six patients with postoperative seromas after varicose vein surgery that were refractory to conventional treatments including compression dressings, repeated needle aspirations and manual lymph drainage. A complete regression of the fluid collections was seen after one and two ultrasound-guided injections of polidocanol foam into the seroma cavity in two cases, respectively. Up to five treatment sessions and up to four further needle aspirations were necessary for the remaining two patients until complete regression of the seromas. No side-effects were reported.|/OTHER TOXICITY INFORMATION/ Treatment of micro-veins of less than 1.5 mm with laser and with chemical sclerosis is technically challenging because of their difficulty to remedy. Laser treatment is even more difficult when dark phototypes are involved.Three groups of 30 patients each, skin type IV, and vessels measuring less than 1.5 mm in diameter, were enrolled for two treatment sessions 8 weeks apart: group A, polidocanol (POL) micro-foam injection; group B, Nd:YAG laser alone; and group C, laser after POL injection. Repeated 8-Hz low-fluence pulses, moving the hand piece over a 3-cm vein segment with an average of five laser passes maximum and with a total time irradiation of 1 s were used. Sixteen weeks after the second treatment, statistically, degree of clearance after examining photographs and patients satisfaction index, plotted on a visual analogue scale and comparing results of all three groups, results were significantly better for group C (p < 0.0001). No significant differences in complications were noticed between the three groups. Efficacy of combining POL and laser proved safe and satisfactory in 96 % of patients using low-fluence laser pulses with a total cumulative energy in the 3 cm venous segment, lower than that of conventional treatment. Very few and transient complications were observed. POL foam injection followed by laser pulses is safe and efficient for vein treatment in dark-skinned patients.

Nonaethylene glycol monododecyl ether Use and Manufacturing

Methods of Manufacturing

Prepared by reaction of ethylene oxide and dodecyl alcohol.

Production

(1984) 1.62X10+9 g|Production volumes for non-confidential chemicals reported under the Inventory Update Rule.[Table#4935]

GRADES OR PURITY: USUALLY 100%

Poly(oxy-1,2-ethanediyl), .alpha.-isotridecyl-.omega.-hydroxy-: ACTIVE|XU - indicates a substance exempt from reporting under the Chemical Data Reporting Rule, (40 CFR 711).|IN GENERAL, COMPD OF THIS TYPE ARE CALLED ALKYL ETHOXYLATES; THEY ARE HIGHLY SURFACE-ACTIVE AND ARE PRESENT IN SOME DETERGENT PRODUCTS.|INSECTICIDAL EFFECT OF POLYOXYETHYLENE LAURYL ETHER (PEL) ON THE HOUSEFLY WAS STUDIED TO CLARIFY ITS USEFULNESS FOR FLY CONTROL AT A WASTE DISPOSAL SITE. LD50 VALUES WERE APPROX 270 AND 260 MUG/FEMALE FOR ORGANOPHOSPHORUS INSECTICIDE-RESISTANT HOKKO COLONY AND FOR THE SUSCEPTIBLE TAKATSUKI STRAIN, RESPECTIVELY. IN THE INDOOR SPRAY, 89.2% WERE KILLED WITH 15-SECOND SPRAY OF 0.3% SOLN, AND ALL WITH 10-SECOND SPRAY OF 0.6% SOLN. IN THE FIELD TEST, THE REDUCTION RATE WAS VERY LOW WHEN THE 0.5% SOLN (1 L/SQ M) WAS SPRAYED AT LOW SPEED OF 0.1 L/SECOND. BUT THE REDUCTION RATES OF 50-91% WERE OBTAINED WHEN SPRAYED AT HIGH SPEED OF 10 L/SECOND.

ALPHA-DODECYL-OMEGA-HYDROXYPOLY(OXY-1,2-ETHANEDIYL) DETERMINED QUANTITATIVELY IN WASTEWATERS FROM MFR OF NONIONIC SURFACTANTS BY OPTICAL REFLECTANCE DENSITY OF CHROMATOGRAPHIC SPOTS @ 480-520 NM, AND BY COLORIMETRY OF COLORED COMPLEXES EXTRACTED WITH CHLOROFORM.|SUBSTITUTED PHENOXYETHANOLS WERE TESTED IN TLC SYSTEMS TO RELATE CHROMATOGRAPHIC BEHAVIOR TO STRUCTURE. A REVERSED-PHASE TLC PROCEDURE WAS DEVELOPED TO RESOLVE POLYETHYLENEGLYCOL FROM VARIOUS NONIONIC SURFACTANTS.

EPA Safer Chemical Functional Use Classes -> Surfactants|Safer Chemical Classes -> Green circle - The chemical has been verified to be of low concern|Human Drugs -> FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book) -> Active Ingredients|Cosmetics -> Emulsifying

Computed Properties

Molecular Weight:582.8
XLogP3:3.9
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:10
Rotatable Bond Count:37
Exact Mass:582.43429817
Monoisotopic Mass:582.43429817
Topological Polar Surface Area:103
Heavy Atom Count:40
Complexity:431
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

Drug Function and Efficacy

Extract from the above information

This ingredient has been used in drugs with the following functions (note: it does not mean that the ingredient itself has the following health functions)

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Registered Holders

  • Nanjing Well Pharmaceutical Group Co., Ltd.

    China China
    Active
  • Jiangsu Jiming Pharmaceutical Technology Co., Ltd.

    China China
    Active
  • Hebei Anjian Chengyi Pharmaceutical Technology Co., Ltd.

    China China
    Active

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