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Grape Seed Oil ( CASNO:8024-22-4 )

Identification and Related Records
Name:
Grape Seed Oil
CAS Registry number:
8024-22-4
Molecular Formula:
C18H32O2
Molecular Weight:
0
Inchi:
InChI=1S/C18H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h6-7,9-10H,2-5,8,11-17H2,1H3,(H,19,20)/b7-6-,10-9-
Canonical SMILES:
CCCCCC=CCC=CCCCCCCCC(=O)O
Isomers smiles:
CCCCC/C=C\C/C=C\CCCCCCCC(=O)O
Chemical and Physical Properties
Melting Point:
-8.5 deg C
Boiling Point:
230 deg C at 16 mm Hg; 202 deg C at 1.4 mm Hg
Solubilities:
Freely sol in ether; sol in absolute alcohol; 1 ml dissolves in 10 ml petroleum ether; miscible with dimethylformamide, fat solvents, oils
Very soluble in acetone, benzene, ethyl ether, and ethanol.
In acetone: 4.10 g/100 g acetone at -50 deg C, 1.20 g/100 g acetone at -60 deg C, 0.35 g/100 g acetone at -70 deg C; in n-heptane: 0.98 g/100 g n-heptane at -50 deg C, 0.20 g/100 g n-heptane at -60 deg C, 0.042 g/100 g n-heptane at -70 deg C.
In water, 0.139 mg/L at 25 deg C (est)
Color/Form:
Colorless oil
Colorless to straw-colored liquid
Spectral properties:
Index of refraction: 1.4715 at 11.5 deg C/D, 1.4699 at 20 deg C/D, 1.4683 at 21.5 deg C/D, 1.4588 at 50 deg C/D
Index of refraction: 1.4710 at 15 deg C
MAX ABSORPTION (ALCOHOL): 232 NM (LOG E= 3.8), 275 NM (LOG E= 2.9); SADTLER REF NUMBER: 914 (IR, PRISM)
IR: 15092 (Sadtler Research Laboratories IR Grating Collection)
1H NMR: 8215 (Sadtler Research Laboratories Spectral Collection)
MASS: 107179 (NIST/EPA/MSDC Mass Spectral database, 1990 verson); 2211 (Atlas of Mass Spectral Data, John Wiley & Sons, New York)
Computed Properties:
Molecular Weight:280.44548 [g/mol]
Molecular Formula:C18H32O2
XLogP3:6.8
H-Bond Donor:1
H-Bond Acceptor:2
Rotatable Bond Count:14
Exact Mass:280.24023
MonoIsotopic Mass:280.24023
Topological Polar Surface Area:37.3
Heavy Atom Count:20
Formal Charge:0
Complexity:267
Isotope Atom Count:0
Defined Atom Stereocenter Count:0
Undefined Atom Stereocenter Count:0
Defined Bond Stereocenter Count:2
Undefined Bond Stereocenter Count:0
Covalently-Bonded Unit Count:1
Feature 3D Acceptor Count:2
Feature 3D Anion Count:1
Feature 3D Hydrophobe Count:2
Effective Rotor Count:14
Conformer Sampling RMSD:1.4
CID Conformer Count:93
Safety and Handling
Skin, Eye, and Respiratory Irritations:
Mild local irritant. Ingestion can cause nausea and vomiting.
Fire Potential:
Combustible
SPONTANEOUS COMBUSTION OF RAGS SOAKED WITH LINSEED OIL & LINOLEIC ACID SALTS PRESENTS FIRE HAZARD.
Formulations/Preparations:
Grade: Technical, purified (99+%), edible.
Exposure Standards and Regulations:
Linoleic acid used as a nutrient and/or dietary supplement in animal drugs, feeds, and related products is generally recognized as safe when used in accordance with good manufacturing or feeding practice.
Substance added directly to human food affirmed as generally recognized as safe (GRAS).
Protective Equipment and Clothing:
Mild local irritant. Ingestion can cause nausea and vomiting.
Octanol/Water Partition Coefficient:
log Kow = 7.05
Disposal Methods:
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.
1. Liquid acid may be injected at base of incinerator or after mixing with a flammable solvent. Afterburner is suggested for complete combustion.
Use and Manufacturing
Use and Manufacturing:
U.S. Production

Production volumes for non-confidential chemicals reported under the Inventory Update Rule. Year Production Range (pounds) 1986 10 thousand - 500 thousand 1990 >1 million - 10 million 1994 >1 million - 10 million 1998 >1 million - 10 million 2002 >10 million - 50 million
9,12-Octadecadienoic acid (9Z,12Z)- 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).
Biomedical Effects and Toxicity
Therapeutic Uses:
/Exptl Ther/ To determine the effect of low doses of linoleic acid and calcium on prostaglandin (PG) levels and the efficacy of this treatment in the prevention of preeclampsia. In a randomized, double-blind, placebo-controlled study we treated 86 primigravidas with risk factors for preeclampsia (high biopsychosocial risk [above 3 points], positive roll-over test, and high mean blood pressure [above 85 mmHg)] with daily doses of either 450 mg linoleic acid and 600 mg calcium (n=43) or 450 mg starch and 600 mg lactose placebo (n=43) during the third trimester of pregnancy. Four women in the experimental group (9.3%) developed preeclampsia compared with 16 (37.2%) controls (relative risk 0.25, 95% confidence interval 0.09, 0.69, P < .001). The median serum levels of PGE2 after 4 weeks of treatment increased by 106% in the experimental group (P=.03) and decreased by 33% in the control group (P=.02). The median ratio between thromboxane B2 and PGE2 decreased by 40% in the experimental group (P=.02) and increased by 18% in the control group (P=.14). No significant differences were observed in the median ratio between thromboxane B2 and 6-keto PGF1alpha in either group. No serious maternal or neonatal side effects of treatment occurred in either group. The administration of low daily doses of linoleic acid and calcium during the third trimester of pregnancy reduced the incidence of preeclampsia significantly in women at high risk, possibly by correcting the PGE2 levels. [Herrera JA et al; Obstet Gynecol 91 (4): 585-90 (1998)]
Environmental Fate and Exposure Potential
Environmental Fate/Exposure Summary:
TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 163,000 for the free acid(SRC), determined from a log Kow of 7.05(2) and a regression-derived equation(3), indicates that undissociated linoleic acid is expected to be immobile in soil(SRC). The pKa of linoleic acid is 4.77(4), indicating that this compound will exist almost entirely in anion form in the environment and anions generally do not adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(5). Volatilization of linoleic acid from moist soil surfaces is not expected to be an important fate process given its ionic state(SRC). Linoleic acid is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 8.68X10-7 mm Hg(6). Linoleic acid reached 9.3% of its theoretical BOD after 6 hours(7), suggesting biodegradation is an important fate process in soil(SRC).
AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 163,000 for the free acid(SRC), determined from a log Kow of 7.05(2) and a regression-derived equation(3), indicates that undissociated linoleic acid is expected to adsorb to suspended solids and sediment(SRC). A pKa of 4.77(4) indicates linoleic acid will exist almost entirely in the anion form at pH values of 5 to 9 and therefore volatilization from water surfaces is not expected to be an important fate process(5). According to a classification scheme(6), an estimated BCF of 10(SRC), from its log Kow(2) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Linoleic acid reached 9.3% of its theoretical BOD after 6 hours(8), suggesting biodegradation is an important fate process in water(SRC).
ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), linoleic acid, which has a vapor pressure of 8.68X10-7 mm Hg at 25 deg C(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase cis- and trans-linoleic acid are degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-lives for these reactions in air are estimated to be 3.0 and 2.7 hours(SRC), respectively, calculated from rate constants of 1.3X10-10 and 1.4X10-10 cu cm/molecule-sec at 25 deg C(SRC) that were derived using a structure estimation method(3). Vapor-phase linoleic acid is also degraded in the atmosphere by reaction with ozone(SRC); the half-lives for cis-linoleic acid and trans-linoleic acid reactions in air are estimated to be 1.1 and 0.7 hours(SRC), respectively, calculated from rate constants of 2.6X10-16 and 4.0X10-16 cu cm/molecule-sec at 25 deg C(SRC) that were derived using a structure estimation method(3). Particulate-phase linoleic acid may be removed from the air by wet or dry deposition(SRC).
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