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Home > Encyclopedia > 1-Tetracosanol

1-Tetracosanol

1-Tetracosanol structure

1-Tetracosanol 

structure
  • CAS No:

    506-51-4

  • Formula:

    C24H50O

  • Chemical Name:

    1-Tetracosanol

  • Synonyms:

    1-Tetracosanol;Lignoceryl alcohol;Lignoceric alcohol;Tetracosyl alcohol;Lignocerol;n-Tetracosanol;Tetracosanol;NSC 93768

  • Categories:

    Pharmaceutical Intermediates  >  Bulk Drug Intermediates

Description

white shiny flakes or fluffy powder


OtherSolid; PelletsLargeCrystals


Tetracosan-1-ol is a very long-chain primary fatty alcohol that is tetracosane in which a hydrogen attached to one of the terminal carbons is replaced by a hydroxy group. It has been isolated from a variety of plants, including grape seeds, evening primrose (Oenothera biennis), pitaya fruits (Hylocereus polyrhizus and Hylocereus undatus), and the flowers of Arabian jasmine (Jasminum sambac). It has a role as a plant metabolite. It is a fatty alcohol 24:0 and a very long-chain primary fatty alcohol. It derives from a hydride of a tetracosane.

1-Tetracosanol Basic Attributes

354.663

354.65

208-043-9

2N0PI37IOC

93768

DTXSID8027161

2905199090

Characteristics

20.2

11.50

OtherSolid; PelletsLargeCrystals

0.8±0.1 g/cm3

76 °C

230-235 °C @ Press: 12 Torr

141.7±5.2 °C

1.456

2.4X10-9 mm Hg at 25 deg C (est)

Henry's Law constant = 2.9X10-3 atm-cu m/mole at 25 °C (est)

Immiscible in water /Decanol and higher fatty alcohols/|Common organic solvents such as petroleum ether, lower alcohols, and diethyl ether are suitable solvents for fatty alcohols. /Fatty alcohols/|Hydroxyl radical reaction rate constant = 3.5X10-11 cu cm/molecule-sec at 25 °C (est)

Safety Information

NONH for all modes of transport

S22-S24/25

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure 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, aquatic, and plant life; and conformance with environmental and public health regulations.

|Danger|H225 (14.29%): Highly Flammable liquid and vapor [Danger Flammable liquids]|P210, P233, P240, P241, P242, P243, P261, P264, P270, P271, P273, P280, P301+P312, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P310, P312, P322, P330, P337+P313, P363, P370+P378, P391, P403+P233, P403+P235, P405, and P501|Aggregated GHS information provided by 122 companies from 8 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

1-Tetracosanol emission rates from wood smoke were calculated as 2.9 ug/g, 0.7 ug/g, and 2.9 ug/g from oak, eucalyptus and pine, respectively(1). 1-Tetracosanol emission rate from road dust samples was 22 ug/g(2). 1-Tetracosanol emission rate from pine wood (Pinus elliottii) smoke was measured at 1163 ng/g of burnt wood(3). 1-Tetracosanol was identified in smoke from the burning of chitin biopolymers(4).

SEDIMENT: 1-Tetracosanol was reported as extractable concentrations of 148 and 254 ng/g and bonded concentrations of 78 and 104 ng/g in anoxic continental slope sediment off southwestern Taiwan(1).

1-Tetracosanol emission rate from cigarettes are 1.1 ug/cigarette(1).

Toxicity

1-Tetracosanol has been found in lanolin(1). 1-Tetracosanol emission rates from green leaf composite samples and dead leaves were 470 ug/g and 240 ug/g, respectively(2).

1-Tetracosanol's production and possible use as a chemical intermediate(1) may result in its release to the environment through various waste streams. It's possible use as a water reservoir evaporation inhibitor(1) would result in its direct release to the environment.

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 5.1X10+5(SRC), determined from a structure estimation method(2), indicates that 1-tetracosanol is expected to be immobile in soil(SRC). Volatilization of 1-tetracosanol from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 2.9X10-3 atm-cu m/mole(SRC), using a fragment constant estimation method(3). However, adsorption to mosit soil is expected to attenuate volatilization(SRC). 1-Tetracosanol is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 2.4X10-9 mm Hg(SRC), determined from a fragment constant method(4). Biodegradation data were not available(SRC, 2006), but long chain linear alcohols are expected to biodegrade(5).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 5.1X10+5(SRC), determined from a structure estimation method(2), indicates that 1-tetracosanol is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(3) based upon an estimated Henry's Law constant of 2.9X10-3 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 6 hours and 7.6 days, respectively(SRC). However, volatilization from water surfaces is expected to be attenuated by adsorption to suspended solids and sediment in the water column. The estimated volatilization half-life from a model pond is 14 years if adsorption is considered(5). According to a classification scheme(6), an estimated BCF of 3(SRC), from an estimated log Kow of 11(7) and a regression-derived equation(8), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Biodegradation data were not available(SRC, 2006), but long chain linear alcohols are expected to biodegrade(8).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 1-tetracosanol, which has an estimated vapor pressure of 2.4X10-9 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase lignoceryl alcohol is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 11 hours(SRC), calculated from its rate constant of 3.5X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Particulate-phase 1-tetracosanol may be removed from the air by wet or dry deposition(SRC).

The rate constant for the vapor-phase reaction of 1-tetracosanol with photochemically-produced hydroxyl radicals has been estimated as 3.5X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 11 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). 1-Tetracosanol is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(2).

An estimated BCF of 3 was calculated for 1-tetracosanol(SRC), using an estimated log Kow of 10.66(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC).

Using a structure estimation method based on molecular connectivity indices(1), the Koc of 1-tetracosanol can be estimated to be 5.1X10+5(SRC). According to a classification scheme(2), this estimated Koc value suggests that 1-tetracosanol is expected to be immobile in soil.

The Henry's Law constant for 1-tetracosanol is estimated as 2.9X10-3 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that 1-tetracosanol is expected to volatilize rapidly from water surfaces(2). Based on this Henry's Law constant, the volatilization half-life from a model river (1 m deep, flowing 1 m/sec, wind velocity of 3 m/sec)(2) is estimated as 6 hours(SRC). The volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec)(2) is estimated as 7.6 days(SRC). However, volatilization from water surfaces is expected to be attenuated by adsorption to suspended solids and sediment in the water column. The estimated volatilization half-life from a model pond is 14 years if adsorption is considered(3). 1-Tetracosanol's Henry's Law constant indicates that volatilization from moist soil surfaces may occur(SRC). 1-Tetracosanol is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 2.4X10-9 mm Hg(SRC), determined from a fragment constant method(4).

NIOSH (NOES Survey 1981-1983) has statistically estimated that 1281 workers (1064 of these are female) are potentially exposed to 1-tetracosanol in the US(1). Occupational exposure to 1-tetracosanol may occur through dermal contact with products containing this compound(SRC). Monitoring data indicate that the general population may be exposed to 1-tetracosanol via inhalation of ambient air and through dermal contact with products containing 1-tetracosanol(SRC).

Drug Information

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/|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/

1-Tetracosanol Use and Manufacturing

Uses

Intermediates

Production

25,000 - 100,000 lb|This chemical is listed as a High Production Volume (HPV) (65FR81686). Chemicals listed as HPV were produced in or imported into the U.S. in >1 million pounds in 1990 and/or 1994. The HPV list is based on the 1990 Inventory Update Rule. (IUR) (40 CFR part 710 subpart B; 51FR21438).

All other basic organic chemical manufacturing|1-Tetracosanol: ACTIVE|Lanolin was saponified and extracted with petroleum ether. The natural fraction of lanolin obtained (wool wax alcohols) was treated with digitonin. After thin-layer chromatography, 5 fractions were isolated from the digitonin-negative fraction from which several steroidal hydrocarbons, including lignoceryl alcohol, were isolated.

Fatty Acyls [FA] -> Fatty alcohols [FA05]

Computed Properties

Molecular Weight:354.7
XLogP3:11.6
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:22
Exact Mass:354.386166214
Monoisotopic Mass:354.386166214
Topological Polar Surface Area:20.2
Heavy Atom Count:25
Complexity:214
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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