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Castor oil(CAS No. 8001-79-4)

Castor oil C18H34O3 (cas 8001-79-4) Molecular Structure

8001-79-4 Structure

Identification and Related Records

【Name】
Castor oil
【CAS Registry number】
8001-79-4
【Synonyms】
Ricinus oil
Castor oil, Pharma
NCI-C55163
Refined castor (Ricinus communis) oil USP
Castor Oil No. 1
Dehydrated Castor Oil Fatty Acid
【EINECS(EC#)】
232-293-8
【Molecular Formula】
C18H34O3 (Products with the same molecular formula)
【Molecular Weight】
298.4608
【Inchi】
InChI=1S/C18H34O3.C18H34O2.C18H32O2/c1-2-3-4-11-14-17(19)15-12-9-7-5-6-8-10-13-16-18(20)21;2*1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h9,12,17,19H,2-8,10-11,13-16H2,1H3,(H,20,21);9-10H,2-8,11-17H2,1H3,(H,19,20);7-10H,2-6,11-17H2,1H3,(H,19,20)/b12-9+;10-9+;8-7+,10-9+
【Canonical SMILES】
CCCCCCCCC=CCCCCCCCC(=O)O.CCCCCCC=CC=CCCCCCCCC(=O)O.CCCCCCC(CC=CCCCCCCCC(=O)O)O
【Isomers smiles】
CCCCCCCC/C=C/CCCCCCCC(=O)O.CCCCCC/C=C/C=C/CCCCCCCC(=O)O.CCCCCCC(C/C=C/
CCCCCCCC(=O)O)O

Chemical and Physical Properties

【Appearance】
Light yellow viscous liquid.
【Density】
0.959
【Melting Point】
-12℃
【Boiling Point】
313℃
【Refractive Index】
n20/D 1.478(lit.)
【Flash Point】
229℃
【Water】
<0.1 g/100 mL at 20 ºC
【Solubilities】
<0.1 g/100 mL at 20 oC
【Color/Form】
Pale-yellowish or almost colorless, transparent, viscous liquid
【Stability】
Stable. Combustible. Incompatible with strong oxidizing agents. May be light sensitive.
【Storage temp】
Store in a tightly closed container. Keep from contact with oxidizing materials. Store in a cool, dry, well-ventilated area away from incompatible substances.
【Spectral properties】
Dextrorotatory (undiluted in sodium light)
Index of refraction: 1.473-1.477 at 25 deg C/D; 1.466-1.473 at 40 deg C/D
Dextrorotary
【Computed Properties】
Molecular Weight:861.3676 [g/mol]
Molecular Formula:C54H100O7
H-Bond Donor:4
H-Bond Acceptor:7
Rotatable Bond Count:44
Exact Mass:860.746906
MonoIsotopic Mass:860.746906
Topological Polar Surface Area:132
Heavy Atom Count:61
Formal Charge:0
Complexity:761
Isotope Atom Count:0
Defined Atom Stereocenter Count:0
Undefined Atom Stereocenter Count:1
Defined Bond Stereocenter Count:4
Undefined Bond Stereocenter Count:0
Covalently-Bonded Unit Count:3

Safety and Handling

【Hazard Codes】
Undergoes spontaneous heating.
【Safety Statements 】
S24/25
【Safety】

An allergen. A human skin and eye irritant. Combustible when exposed to heat. Spontaneous heating may occur. To fight fire, use CO2, dry chemical, fog, mist.

【Skin, Eye, and Respiratory Irritations】
A human skin and eye irritant.
Castor oil was mildly irritating to the skin of human subjects.
May cause respiratory tract irritation. May cause skin irritation. May cause eye irritation.
【Cleanup Methods】
SRP: Wastewater from contaminant suppression, cleaning of protective clothing/equipment, or contaminated sites should be contained and evaluated for subject chemical or decomposition product concentrations. Concentrations shall be lower than applicable environmental discharge or disposal criteria. Alternatively, pretreatment and/or discharge to a permitted wastewater treatment facility is acceptable only after review by the governing authority and assurance that "pass through" violations will not occur. Due consideration shall be given to remediation worker exposure (inhalation, dermal and ingestion) as well as fate during treatment, transfer and disposal. If it is not practicable to manage the chemical in this fashion, it must be evaluated in accordance with EPA 40 CFR Part 261, specifically Subpart B, in order to determine the appropriate local, state and federal requirements for disposal.
Spillages are slippery and should be covered with an inert absorbant before collection and disposal.
Personal precautions: Avoid breathing vapors, mist or gas.
Environmental precautions: Do not let product enter drains.
Methods for cleaning up: Keep in suitable, closed containers for disposal.
【Fire Fighting Procedures】
To fight fire, use /carbon dioxide/, dry chemical, fog, mist.
Suitable extinguishing media: Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.
Special protective equipment for fire-fighters: Wear self contained breathing apparatus for fire fighting if necessary.
【Fire Potential】
Combustible when exposed to heat. Spontaneous heating may occur.
【Formulations/Preparations】
EmCon CO
Lipovol CO
Official preparations are castor oil, USP, and aromatic castor oil, NF. Although the objectionable taste of the oil is partially masked in the latter preparation, flavored castor oil emulsions are somewhat more palatable.
Grades: USP Number 1; Number 3; Refined; FCC.
Fatty acid composition is approx ricinoleic 87%, oleic 7%, linoleic 3%, palmitic 2%, stearic 1%, and dihydroxystearic trace amounts.
Castor oil quality and specifications prescribed by the International Castor Oil Association, Inc.: pale oil, No. 1 oil, No. 2 oil, and No. 3 oil.
If chilled castor oil is taken with fruit juice or a carbonated beverage is consumed immediately thereafter, tolerance is improved. Neoloid, a mint-flavored emulsion of castor oil, also may be more palatable.
【Exposure Standards and Regulations】
The following substances may be safely used as diluents in color additive mixtures for food use exempt from certification, subject to the condition that each straight color in the mixture has been exempted from certification or, if not so exempted, is from a batch that has previously been certified and has not changed in composition since certification. If a specification for a particular diluent is not set forth in this part 73, the material shall be of a purity consistent with its intended use. (a) General use. (1) Substances that are generally recognized as safe under the conditions set forth in section 201(s) of the act. (2) Substances meeting the definitions and specifications set forth under subchapter B of this chapter, and which are used only as prescribed by such regulations. ... Substance: Castor oil; Definitions and specifications: As set forth in U.S.P. XVI; Restrictrions: Not more than 500 p.p.m. in the finished food. Labeling of color additive mixtures containing castor oil shall bear adequate directions for use that will result in a food meeting this restriction.
The food additive castor oil may be safely used in accordance with the following conditions: (a) The additive meets the specifications of the United States Pharmacopeia XX (1980). (b) The additive is used or intended for use as follows: Use and Limitations: Hard candy production -- As a release agent and antisticking agent, not to exceed 500 parts per million in hard candy; Vitamin and mineral tablets -- As a component of protective coatings.
Natural flavoring substances and natural adjuvants may be safely used in food in accordanace with the following conditions. (a) They are used in the minimum quantity required to produce their intended physical or technical effect and in accordance with all the principles of good manufacturing practice. (b) In the appropriate forms (plant paarts, fluid and solid extracts, concretes, absolutes, oils, gums, balsams, resins, oleoresins, waxes, and distillates) they consist of one or more of the following, used alone or in combination with flavoring substances and adjuvants generally recognized as safe in food, previously sanctioned for such use, or regulated in any section of this part. Castor oil in included on this list.
The Generic Animal Drug and Patent Restoration act requires that each sponsor of an approved animal drug must submit to the FDA certain information regarding patents held for the animal drug or its method of use. The Act requires that this information, as well as a list of all animal drug products approved for safety and effectiveness, be made available to the public. Castor oil is included on this list.
【Reactivities and Incompatibilities】
Incompatible with strong oxidizing agents.
Materials to avoid: Strong oxidizing agents.
【Other Preventative Measures】
SRP: The scientific literature for the use of contact lenses by industrial workers is inconsistent. The benefits or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.
Handling: Normal measures for preventive fire protection.
In case of skin contact: Wash off with soap and plenty of water.
In case of eye contact: Flush eyes with water as a precaution.
Hygiene measures: General industrial hygiene practice.
【Protective Equipment and Clothing】
Respiratory protection: Respiratory protection is not required. Where protection is desired, use multi-purpose combination (US) or type ABEK (EN 14387) respirator cartridges. Use respirators and components tested and approved under appropriate government standards such as NIOSH (US) or CEN (EU).
Hand protection: For prolonged or repeated contact use protective gloves.
Eye protection: Safety glasses.
【Specification】

Background of?Castor oil (CAS NO.8001-79-4):
Structure of the major component of castor oil.Ricinoleic acid, a monounsaturated, 18-carbon fatty acid, is unusual in that it has a hydroxyl functional group on the twelfth carbon. This functional group causes ricinoleic acid (and castor oil) to be unusually polar, and also allows chemical derivatization that is not practical with most other seed oils. It is the hydroxyl group which makes castor oil and ricinoleic acid valuable as chemical feedstocks. Compared to other seed oils which lack the hydroxyl group, castor oil commands a higher price.

【Report】

CASTOR OIL is reported in EPA TSCA Inventory.

【Disposal Methods】
SRP: Criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.
Observe all federal, state, and local environmental regulations.

Use and Manufacturing

【Use and Manufacturing】
Methods of Manufacturing

Obtained from castor beans (Ricinus communis) by pressing and/or solvent extraction, followed by refining, deodorizing or decolorizing
From the seeds of the castor bean, Ricinus communis, ... They are cold-pressed for the first grade of medicinal oil and hot pressed for the common qualities, approximately 40% of the oil content of the bean being obtained. Residual oil in the cake is obtained by solvent extraction.
Cold pressing of the spotted, oblong seeds yields a light, viscous oil which is used primarily in pharmaceutical products. Subsequent expelling at elevated temperatures and extraction with hexane yields a yellowish-brown oil which is used primarily in technical applications.
U.S. Exports

(1972) 1.51 X 10+9 g - Including palm and palm kernel oil
(1975) 2.42 X 10+9 g - Including palm and palm kernel oil
(1984) 1.93 X 10+9 g /Castor oil, palm, and palm kernel oil, unmixed/
U.S. Imports

(1972) 4.45 X 10+10 g
(1975) 3.12 X 10+10 g
(1984) 3.54 X 10+10 g
U.S. Production

(1972) 1.36 X 10+9 g
(1975) 4.54 X 10+8 g
(1984) No current US production
Castor oil is listed as a High Production Volume (HPV) chemical (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).
Production volumes for non-confidential chemicals reported under the Inventory Update Rule. Year Production Range (pounds) 1986 >10 million - 50 million 1990 >10 million - 50 million 1994 >50 million - 100 million 1998 >50 million - 100 million 2002 >50 million - 100 million
Production volume for non-confidential chemicals reported under the 2006 Inventory Update Rule. Chemical: Castor oil. Aggreated National Production Volume: 10 to
Consumption Patterns

7% in resins and plastics; 6% for dehydrated castor oil used as a drying oil in paints and varnishes; 5% in lubricants and similar oils; 2.5% as chemical intermediate for fatty acids; and 79.5% for all other uses (1973)
Paint (includes caulks and sealants), 40%; Lubricants, 30%, Textiles (includes sulfated castor oil), 20%; Plasticizers & Synthetic Lubricants, 5%; Urethanes, 3%; Cosmetics and Pharmaceuticals, 2% (1984)
【Usage】

Rodenticide, insecticide, insect repellent.

Biomedical Effects and Toxicity

【Pharmacological Action】
If ingested causes severe diarrhea.
【Therapeutic Uses】
Cathartics; Emollients; Pharmaceutic Aids
Therapeutically, castor oil has been administered orally for its laxative action... /Former use/
Castor oil is used in cosmetics and foods and orally, parenterally, and topically in pharmaceutical formulations. It is generally regarded as a relatively nontoxic and nonirritant material when used as an excipient.
...It is usually administered only when prompt, thorough evacuation of the bowel is desired, as in preparation for certain radiological examinations. /Former/
The usual cathartic dose /of castor oil/ (in adults, 15-60 mL on an empty stomach) produces one or two copious and semifluid stools within 1-6 hr. Thus, castor oil should not be taken late in the day with the expectation of sleeping.
If chilled castor oil is taken with fruit juice or a carbonated beverage is consumed immediately thereafter, tolerance is improved. Neoloid, a mint-flavored emulsion of castor oil, also may be more palatable.
It is ... used to empty the GI tract of gas and feces prior to proctoscopy or X-ray studies of GI tract ...sometimes employed to initiate labor at term. Hyperemia of intestinal tract causes reflex stimulation of uterus. /Former/
No harm results if this dose (usually 15 mL) is exceeded inasmuch as the cathartic action of the first portion of the oil sweeps the remaining oil through intestinal tract.
Medication (Veterinary): As a laxative or purgative in non-ruminants or young ruminants, where saponification in small intestine helps produce a small amount of an irritant sodium ricinoleate soap which produces most of desired effect. This occurs within approx 4-6 hr in dogs and longer ... in large animals (12 hr in calves and foals).
Medication (Veterinary): The balance of the oil produces bulk enhancing and lubricating effects. Part of this is due to formation of glycerine from hydrolysis of part of castor oil. Still /as of 1974/ popular oral treatment of calves and foals for meconium retention.
Medication (Vet): Externally, it is used like other bland oils in zinc oxide-type ointments, ulcer therapy, and to aid epitheliazation of burn-like lesions without dessication and cornification. Alone or with thuja by daily application for the removal of teat warts on cows.
Medication (Vet): Topically, as a corneal protectant after foreign body injuries, and as a vehicle for prolonged action of alkaloids such as cocaine and atropine on the eye.
The use of castor oil to stimulate labor /was investigated/ using 196 patients with premature rupture of membranes (PROM), at least 4 hr in duration, who were between 37 and 42 weeks of gestation. Patients were identified by reviewing charts of all patients who were admitted at an out-of-hospital birthing center from 1976 through 1981. Of the 196 patients, 107 (mean age = 28.6 years) were dosed orally with castor oil (2 oz) and 89 (mean age=27.6 years) were not. Castor oil was administered only to PROM patients who had a latency period of at least 4 hr. All patients were observed for labor onset for 24 hr after the onset of PROM. If labor did not occur at this time, the patients were transferred to a hospital for oxytocin stimulation. The longest interval between rupture of the membranes and delivery was 48 hr. Of the 107 patients dosed with castor oil, 80 (75%) had labor onset. Spontaneous labor occurred in 52 (58%) of the 89 control patients. This difference between patients dosed with castor oil and controls was statistically significant (p < .05). The interval between castor oil administration and the onset of labor ranged from 1 to 13 hr (mean = 4 hr). Labor outcomes were also evaluated for type of delivery, incidence of oxytocin stimulation, and infant well-being. The need for cesarean sections was nearly three times greater in the control group (15.7% incidence) than in patients dosed with castor oil (5.6% incidence). This difference was found to be statistically significant (p < .01). Additionally, the group dosed with castor oil did not require oxytocin stimulation as frequently (36% incidence) when compared to the control group (43% incidence), and the difference was not statistically significant. Infant outcomes in the two groups were studied by observing Apgar scores at 1 and 5 min, and looking for any evidence of meconium staining. Two infants with Apgar scores of <7 were reported for both groups. At the time of membrane rupture, the presence of meconium was very low in both groups. Meconium staining was not observed after dosing with castor oil. It is also important to note that there were no maternal deaths and no significant maternal morbidity.
【Biomedical Effects and Toxicity】
... Some absorption of its intestinal metabolites occurs before the intestine is cleared.
Ricinoleate, like other anionic surfactants, reduces net absorption of fluid and electrolytes and stimulates intestinal peristalsis. Ricinoleic acid also is absorbed and metabolized like other fatty acids.
Two rabbits (weight = 3 kg) were fed 6% castor oil in the diet for 18 days; fecal collection occurred during the last ten days. The utilization (uncorrected for metabolic fat) of castor oil was 92.1%, which /was/ considered to be efficient utilization. For both rabbits, the percentage of fat in the feces was 2.2%.
Adult rats (number, weights, and strain not stated) received a diet containing 48.4% castor oil for 4 to 6 weeks. Control rats received stock ration only. Feces were collected from three rats on the castor oil diet. At the end of the feeding period, excised organs/tissues were ground thoroughly and samples of phospholipid fatty acids were obtained from the liver, small intestine, and muscle; glyceride fatty acids were obtained from the liver and fat depots. There was no evidence of catharsis in any of the animals. Average percentages of Ricinoleic Acid in the phospholipid fatty acids were as follows: liver (test: 1.3 +/- 0.6% [9 analyses]; controls: 1.7 +/- 1.1% [7 analyses]), small intestine (test: 4.9 +/- 1.7% [8 analyses]; controls: 6.0 +/- 4.4% [4 analyses]), and skeletal muscle (test: 3.6 +/- 2.9% [8 analyses]; controls: 4.0 +/- 1.7% [7 analyses]). The following values are average percentages of Ricinoleic Acid in glycerides and cholesterol esters: fat depots (test: 6.8 +/- 4.2% [11 analyses]; controls: 0.5 +/- 0.5% [7 analyses]) and liver (test: 7.2 +/- 2.4% [8 analyses]; controls: 5.6 +/- 4.1% [5 analyses]). /It was/ concluded that the feeding of castor oil did not lead to the appearance of significant amounts of Ricinoleic Acid in phospholipids of the small intestine, liver, and skeletal muscle, nor in glycerides of the liver. Additionally, they concluded that ricinoleic acid is a component acid of the glycerides in the fat depots, comprising 7% of the total fatty acids. The fatty acids excreted by each of three rats amounted to 2.1%, 2.2%, and 3.6% of those ingested. Total body fat in these three animals was also determined, and it was calculated that 1% to 2% of absorbed Ricinoleic Acid was deposited in the fat depots. /It was/ concluded that Ricinoleic Acid was rapidly metabolized.
The digestion, absorption, and metabolism of castor oil (medicinal grade) /was studied/ in eight male Sprague-Dawley rats (weights=100 to 200 g). The composition of the castor oil was as follows: ricinoleic acid (90.0%), linoleic acid (4.7%), oleic acid (3.2%), stearic acid (1.0%), palmitic acid (1.0%), and palmitoleic acid (0.1%). In the first experiment, four rats were fed rat chow ad libitum, and the remaining four were fasted overnight. On the following morning, castor oil (1.0 mL) was dosed via stomach tube and chyle was collected over a 24- hr period. The mean values for percent recovery of Ricinoleic Acid in fasted and fed rats were 6.8% and 24.2%, respectively (p
Two groups of five male Wistar rats (3 weeks old) received 10% castor oil in the diet (cholesterol-enriched and cholesterol-free, respectively) for 20 days. In both dietary groups, a very small quantity of Ricinoleic Acid was present in perirenal adipose tissue, but not in the serum or hepatic tissue. It was also noted that the perirenal fatty acid profiles did not reflect those of the dietary fats, either in the absence or presence of dietary cholesterol. The fecal recovery of Ricinoleic Acid was approximately 0.5% of the total ingested. It was concluded that castor oil was readily absorbed and metabolized.
The absorption and excretion of castor oil /was studied/ in five subjects (ages and weights not stated). The composition of the castor oil was as follows: palmitic acid (1%), palmitoleic acid (0.1%), stearic acid (1%), oleic acid (3.2%), linoleic acid (4.7%), and Ricinoleic Acid (90%). The castor oil (of medicinal purity) contained a trace amount of oil labelled with 131I, and the doses administered ranged from 4 to 60 g (approximately 6 uCi of radioactivity per dose). Castor oil was administered to the five hypertensive patients on the day before a scheduled intravenous pyelogram; thereafter, only a light meal of coffee and toast was allowed. Stool collections were made during the first 24 hr after dosing and during the subsequent 72 hr. Urine was collected in 24-hr samples. Small doses of oil were administered to the three normal volunteers, and free diet was allowed. Stools were collected at 2 and 3 days after dosing. Fecal recovery of 131I (%) ranged from 11.4% (for 10 g dose of castor oil) to 86.0% (for 44.4 g dose of castor oil).

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