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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
Stereochemistry ABSOLUTE
Additional Stereochemistry
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

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
PubMed

PubMed

TitleDatePubMed
The direct effect of injectable cyclosporine and its vehicle, cremophor, on endothelial vascular cell adhesion molecule-1 expression. Ricinoleic acid inhibits coronary artery endothelial activation.
1995 Aug 15
First "hybrid" ligands of vanilloid TRPV1 and cannabinoid CB2 receptors and non-polyunsaturated fatty acid-derived CB2-selective ligands.
2006 Jan 23
Patents

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
Created
by admin
on Tue Oct 22 08:37:29 UTC 2019
Edited
by admin
on Tue Oct 22 08:37:29 UTC 2019
Record UNII
I2D0F69854
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
RICINOLEIC ACID
HSDB   INCI   MART.   MI   VANDF   WHO-DD  
INCI  
Official Name English
NSC-281242
Code English
RICINOLEIC ACID [HSDB]
Common Name English
RICINOLEIC ACID [WHO-DD]
Common Name English
(9Z,12R)-12-HYDROXY-9-OCTADECENOIC ACID
Systematic Name English
RICINOLEIC ACID [MART.]
Common Name English
D-12-HYDROXYOLEIC ACID
Common Name English
RICINOLEATE
Systematic Name English
RICINOLEIC ACID [VANDF]
Common Name English
(9Z,12R)-12-HYDROXYOCTADEC-9-ENOIC ACID
Systematic Name English
RICINOLEIC ACID [MI]
Common Name English
RICINOLEIC ACID [INCI]
Common Name English
Code System Code Type Description
PUBCHEM
643684
Created by admin on Tue Oct 22 08:37:30 UTC 2019 , Edited by admin on Tue Oct 22 08:37:30 UTC 2019
PRIMARY
WIKIPEDIA
RICINOLEIC ACID
Created by admin on Tue Oct 22 08:37:30 UTC 2019 , Edited by admin on Tue Oct 22 08:37:30 UTC 2019
PRIMARY
EPA CompTox
141-22-0
Created by admin on Tue Oct 22 08:37:30 UTC 2019 , Edited by admin on Tue Oct 22 08:37:30 UTC 2019
PRIMARY
HSDB
141-22-0
Created by admin on Tue Oct 22 08:37:30 UTC 2019 , Edited by admin on Tue Oct 22 08:37:30 UTC 2019
PRIMARY
ECHA (EC/EINECS)
205-470-2
Created by admin on Tue Oct 22 08:37:30 UTC 2019 , Edited by admin on Tue Oct 22 08:37:30 UTC 2019
PRIMARY
CAS
141-22-0
Created by admin on Tue Oct 22 08:37:30 UTC 2019 , Edited by admin on Tue Oct 22 08:37:30 UTC 2019
PRIMARY
RXCUI
35605
Created by admin on Tue Oct 22 08:37:30 UTC 2019 , Edited by admin on Tue Oct 22 08:37:30 UTC 2019
PRIMARY
EVMPD
SUB129680
Created by admin on Tue Oct 22 08:37:30 UTC 2019 , Edited by admin on Tue Oct 22 08:37:30 UTC 2019
PRIMARY
MESH
C030521
Created by admin on Tue Oct 22 08:37:30 UTC 2019 , Edited by admin on Tue Oct 22 08:37:30 UTC 2019
PRIMARY
MERCK INDEX
M9605
Created by admin on Tue Oct 22 08:37:30 UTC 2019 , Edited by admin on Tue Oct 22 08:37:30 UTC 2019
PRIMARY Merck Index
RXCUI
618482
Created by admin on Tue Oct 22 08:37:30 UTC 2019 , Edited by admin on Tue Oct 22 08:37:30 UTC 2019
ALTERNATIVE
Related Record Type Details
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
PARENT->INNOVATOR
SALT/SOLVATE -> PARENT
LIPID -> FATTY ACID
Related Record Type Details
ACTIVE MOIETY