U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C18H34O3
Molecular Weight 298.4608
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of RICINOLEIC ACID

SMILES

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

InChI

InChIKey=WBHHMMIMDMUBKC-QJWNTBNXSA-N
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

HIDE SMILES / InChI

Molecular Formula C18H34O3
Molecular Weight 298.4608
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 1
Optical Activity UNSPECIFIED

Description

The oil obtained from the seeds of the castor oil plant Ricinus communis is one of the oldest drugs known to man. Castor oil is known primarily as an effective laxative; however, it was also used in ancient times with pregnant women to induce labor. Aside from getting rid of acne, castor oil also helps detoxify the skin. It helps break up the oils that clog glands and pores on the face. Only now, have scientists at the Max Planck Institute for Heart and Lung Research succeeded in unravelling the mysteries of the action mechanism. Ricinoleic acid released from the oil in the intestine, is responsible for the analgesic and anti-inflammatory effects. It was discovered, that G protein-coupled receptors, a large group of receptors in the body involved primarily in transmitting signals in cells. Hundreds of receptors were systematically turned off, and then the reaction of the cells to ricinoleic acid was tested. Ultimately, was succeeded identified the key receptor with the name EP3. There was concluded that after being released from the castor oil, the ricinoleic acid is first of all absorbed by the body via the intestinal mucosa; the EP3 receptor then becomes active on the muscle cells of the intestine and uterus, which in turn stimulates intestinal activity.

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
Unknown

Sample Use Guides

In Vivo Use Guide
for mice: 0.9 mg/mouse
Route of Administration: Topical
In Vitro Use Guide
Ricinoleic acid and several structurally related compounds were tested for their effects on the smooth muscle contractions of the coaxially stimulated guinea-pig ileum, the spontaneously contracting rabbit jejunum, 90 mM potassium depolarized guinea-pig taenia coli and rat colon. In concentrations of 1.25 X 10(-5) to 4 X 10(-4) M, ricinoleate produced a dose-dependent depression of the stimulated guinea-pig ileum.
Substance Class Chemical
Record UNII
I2D0F69854
Record Status Validated (UNII)
Record Version