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Ricinoleic Acid

Synopsis, Chemistry

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Also known as: 141-22-0, Ricinolic acid, Ricinic acid, (r,z)-12-hydroxyoctadec-9-enoic acid, Castor oil acid, 12-hydroxy-cis-9-octadecenoic acid

Molecular Formula

C₁₈H₃₄O₃

Molecular Weight

298.5 g/mol

InChI Key

WBHHMMIMDMUBKC-QJWNTBNXSA-N

FDA UNII

I2D0F69854

ricinoleic acid is a natural product found in Ipomoea cuneata, Cephalocroton cordofanus, and other organisms with data available.

1 2D Structure

Ricinoleic Acid

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(Z,12R)-12-hydroxyoctadec-9-enoic acid

2.1.2 InChI

InChI=1S/C18H34O3/c1-2-3-4-11-14-17(19)15-12-9-7-5-6-8-10-13-16-18(20)21/h9,12,17,19H,2-8,10-11,13-16H2,1H3,(H,20,21)/b12-9-/t17-/m1/s1

2.1.3 InChI Key

WBHHMMIMDMUBKC-QJWNTBNXSA-N

2.1.4 Canonical SMILES

CCCCCCC(CC=CCCCCCCCC(=O)O)O

2.1.5 Isomeric SMILES

CCCCCC[C@H](C/C=C\CCCCCCCC(=O)O)O

2.2 Other Identifiers

2.2.1 UNII

I2D0F69854

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 12-d-hydroxy-9-trans-octadecenoic Acid

2. 12-hydroxy-9-octadecenic Acid

3. 12-hydroxy-9-octadecenoic Acid

4. 12-hydroxyoctadec-cis-9-enoic Acid

5. 9-octadecenoic Acid, 12-hydroxy-, (9e,12r)-

6. Ricinelaidic Acid

7. Ricinoleic Acid, (r-(e))-isomer

2.3.2 Depositor-Supplied Synonyms

1. 141-22-0

2. Ricinolic Acid

3. Ricinic Acid

4. (r,z)-12-hydroxyoctadec-9-enoic Acid

5. Castor Oil Acid

6. 12-hydroxy-cis-9-octadecenoic Acid

7. D-12-hydroxyoleic Acid

8. (9z,12r)-12-hydroxyoctadec-9-enoic Acid

9. Kyselina Ricinolova

10. Oleic Acid, 12-hydroxy-

11. Nouracid Cs 80

12. 9-octadecenoic Acid, 12-hydroxy-, [r-(z)]-

13. Kyselina 12-hydroxy-9-oktadecenova

14. L'acide Ricinoleique

15. 12-hydroxyoleic Acid

16. Nsc 281242

17. 9-octadecenoic Acid, 12-hydroxy-, (9z,12r)-

18. Chebi:28592

19. 12-hydroxyoctadeca-9-enoic Acid

20. 12r-hydroxy-9z-octadecenoic Acid

21. 12-d-hydroxy-9-cis-octadecenoic Acid

22. I2d0f69854

23. 12-hydroxy-9-octadecenoic Acid

24. (r)-12-hydroxy-cis-9-octadecenoic Acid

25. Fatty Acids, Castor-oil

26. 9-octadecenoic Acid, 12-hydroxy-, (r-(z))-

27. Dsstox_cid_21567

28. Dsstox_rid_79777

29. Dsstox_gsid_41567

30. Riconoleic Acid

31. 61789-44-4

32. Ricinoleic Acid (purity Inverted Exclamation Marky99%)

33. Ricinusoleic Acid

34. Acide Ricinoleique

35. [r]-12-hydroxy-cis-9-octadecenoic Acid

36. Cas-141-22-0

37. Ncgc00161336-02

38. (cis,r)-12-hydroxyoctadec-9-enoic Acid

39. Acide Ricinoleique [french]

40. Kyselina Ricinolova [czech]

41. Ricinolsaeure

42. Ricinoleic-acid

43. 9-octadecenoic Acid, 12-hydroxy-

44. L'acide Ricinoleique [french]

45. Unii-i2d0f69854

46. Hsdb 5634

47. Nsc-281242

48. 9-octadecenoic Acid,12-hydroxy-,(z)-

49. Ncgc00181322-01

50. Einecs 205-470-2

51. Mfcd00084840

52. Vespula Pensylvanica B708568k062

53. (9z,12r)-12-hydroxy-9-octadecensaeure

54. (r-(z))-12-hydroxy-9-octadecenoic Acid

55. (z,12r)-12-hydroxyoctadec-9-enoic Acid

56. 9-octadecenoic Acid, 12-hydroxy-, (z)-

57. Ai3-17956

58. (9z,12r)-12-hydroxy-9-octadecenoic Acid

59. Unii-kd8t3w6vzx

60. 9-octadecenoic Acid, 12-hydroxy-, (cis)-

61. Kyselina 12-hydroxy-9-oktadecenova [czech]

62. Kd8t3w6vzx

63. Ricinoleic Acid, >=99%

64. Schembl18144

65. Flexricin 100 (salt/mix)

66. Ricinoleic Acid [mi]

67. Ricinoleic Acid [hsdb]

68. Ricinoleic Acid [inci]

69. Bml2-f10

70. Ricinoleic Acid [vandf]

71. 9-octadecenoicacid,12-hydroxy-

72. Chembl3186422

73. Dtxsid0041567

74. Ricinoleic Acid [mart.]

75. Hy-n6070a

76. Ricinoleic Acid [who-dd]

77. Hy-n6070

78. 12-hydroxy-9(z)-octadecenoic Acid

79. Ricinoleic Acid, Analytical Standard

80. Tox21_113406

81. Tox21_301098

82. Lmfa02000184

83. Zinc12954494

84. 12r-hydroxy-9-cis-octadecenoic Acid

85. Akos016005826

86. (9z)-(12r)-hydroxyoctadecenoic Acid

87. Db02955

88. (z,r)-12-hydroxyoctadec-9-enoic Acid

89. 12-oh 9c-18:1

90. Ncgc00161336-01

91. Ncgc00161336-03

92. Ncgc00181089-01

93. Ncgc00254998-01

94. (9z)-12-hydroxy-9-octadecenoic Acid #

95. As-65782

96. Cs-0032307

97. Cs-0204122

98. R0027

99. C08365

100. Ricinoleic Acid, Vetec(tm) Reagent Grade, 80%

101. A885691

102. Q424484

103. 9-octadecenoic Acid, 12-hydroxy-, (theta-(z))-

104. W-108189

2.4 Create Date

2004-09-16

3 Chemical and Physical Properties

Molecular Formula	C₁₈H₃₄O₃
Molecular Weight	298.5 g/mol
XLogP3	5.7
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	3
Rotatable Bond Count	15
Exact Mass	298.25079494 g/mol
Monoisotopic Mass	298.25079494 g/mol
Topological Polar Surface Area	57.5 Å²
Heavy Atom Count	21
Formal Charge	0
Complexity	261
Isotope Atom Count	0
Defined Atom Stereocenter Count	1
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	1
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Minimum/Potential Fatal Human Dose

2. 2= Slightly toxic, Probable oral lethal dose (human) is 5-15 g/kg, between 1 pint and 1 quart for 70 kg person (150 lb).

Gosselin, R.E., H.C. Hodge, R.P. Smith, and M.N. Gleason. Clinical Toxicology of Commercial Products. 4th ed. Baltimore: Williams and Wilkins, 1976., p. II-134

The lowest dose at which mortality occurred following an accidental ingestion was 5000 mg/kg.

Clayton, G. D. and F. E. Clayton (eds.). Patty's Industrial Hygiene and Toxicology: Volume 2A, 2B, 2C: Toxicology. 3rd ed. New York: John Wiley Sons, 1981-1982., p. 4967

5 Pharmacology and Biochemistry

5.1 Absorption, Distribution and Excretion

Ricinoleic acid or methyl ricinoleate was administered via gastric intubation to male rats (minimum weight of 400 g) with a cannulated thoracic duct. Lymph was collected for 48 hr, and the lipids were then extracted and separated into various lipid classes. Results indicated that Ricinoleic acid was present in the triglyceride, diglyceride, monoglyceride, and free fatty acid fractions. Peak absorption of ricinoleic acid occurrred within 30 min post administration. Ricinoleic acid was not present in the phospholipid or cholesterol ester fractions of the lymph lipids.

Cosmetic Ingredient Expert Review Panel; Final Report on the Safety Assessment of Ricinus Communis (Castor) Seed Oil, Hydrogenated Castor Oil, Glyceryl Ricinoleate, Glyceryl Ricinoleate SE, Ricinoleic Acid, Potassium Ricinoleate, Sodium Ricinoleate, Zinc Ricinoleate, Cetyl Ricinoleate, Ethyl Ricinoleate, Glycol Ricinoleate, Isopropyl Ricinoleate, Methyl Ricinoleate, and Octyldodecyl Ricinoleate; International Journal of Toxicology 26 (3 Suppl): 31-77 (2007).

The skin penetration of ricinoleic acid in vivo /was investigated/ using rats that were 20 to 30 days old. In order to increase the fluorescence of ricinoleic acid, either one part of methyl anthranilate or methylcholanthrene was added to 99 parts ricinoleic acid. The test substance was gently rubbed on to skin that had been clipped free of hair. Biopsies were taken at various intervals post application. The preparations were observed using a Spencer microscope with a quartz condenser. Ricinoleic acid was retained mainly in the outer strata of the epidermis. There was little evidence of deeper penetration in biopsies that were taken at 2 hr post application.

The percutaneous absorption of a radiolabeled (3H)ricinoleic acid (specific activity = 20.0 mCi/mmol) mixture was evaluated using porcine skin membranes or silastic (polydimethylsioloxane) membranes in the Bronaugh flow-through diffusion cell system. [3H]Ricinoleic acid (5%) mixtures were prepared in water containing either 5% mineral oil or 5% PEG 200. Other (3H)Ricinoleic acid mixtures were formulated with the following three commonly used cutting fluid additives: triazine, linear alkylbenzene sulfonate, and triethanolamine. At 8 hr after topical exposure, Ricinoleic acid absorption (based on amount recovered in receptor fluid) ranged from 1% to 13% in silastic membranes and 0.1% to 0.3% in porcine skin membranes. For most mixtures, peak absorption of ricinoleic acid occurred within 3 hr. The greatest ricinoleic acid peak concentrations were associated with the control mixtures containing PEG in both membranes.

/Investigators/ studied the accumulation of hydroxyl acids in depot fat after rats were fed with ricinoleic acid in two experiments. In the first experiment, adult male rats (number, strain, and weights not stated) were fed ricinoleic acid (5% emulsion, 20 mL) for 7 days. In the second experiment, the animals were fed for 27 days. Lipid extraction from the fat tissue was followed by hydrolysis to yield a fatty acid mixture. A gas-liquid chromatogram indicated appreciable amounts of the following hydroxy fatty acids with shorter chain lengths than ricinoleic acid: 10-hydroxyhexadecenoic acid (experiment 1: 0.60% of total fatty acids; experiment 2: 0.33% of total fatty acids), 8-hydroxytetradecenoic acid (experiment 1: 0.03% of total fatty acids; experiment 2: 0.08% of total fatty acids), and 6-hydroxydodecenoic acid (experiment 2: 0.03% of total fatty acids). Ricinoleic acid comprised 0.51% of total fatty acids in experiment 1 and 3.85% of total fatty acids in experiment 2.

For more Absorption, Distribution and Excretion (Complete) data for Ricinoleic acid (9 total), please visit the HSDB record page.

5.2 Metabolism/Metabolites

Three healthy subjects /were/ administered castor oil (10 to 15 mL) orally. Urine was collected between 2 and 8 hr post dosing. The following three epoxydicarboxylic acids were excreted in the urine: 3,6-epoxyoctanedioic acid; 3,6-epoxydecanedioic acid; and 3,6-epoxydodecanedioic acid. These three ricinoleic acid metabolites were also detected in the urine of rats...