Sodium ricinoleate

Sodium ricinoleate is the sodium salt of ricinoleic acid, the principal fatty acid derived from castor oil.[1] It is used in making soap, where its molecular structure causes it to lather more easily than comparable sodium soaps derived from fatty acids.[1] It is a bactericide.[2] It exhibits several polymorphic structural phases.[3]

Sodium ricinoleate

Names
Preferred IUPAC name Sodium (9Z,12R)-12-hydroxyoctadec-9-enoate
Other names Ricinoleic acid sodium salt
Identifiers
CAS Number	5323-95-5 Y
3D model (JSmol)	Interactive image
ChemSpider	17215848
ECHA InfoCard	100.023.811
EC Number	226-191-2
PubChem CID	23687338
RTECS number	VJ3500000
UNII	OOO64813BX Y
CompTox Dashboard (EPA)	DTXSID9026005
InChI InChI=1S/C18H34O3.Na/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);/q;+1/p-1/b12-9-;/t17-;/m1./s1 Key: IJRHDFLHUATAOS-DPMBMXLASA-M
SMILES O[C@H](CCCCCC)C/C=C\CCCCCCCC([O-])=O.[Na+]
Properties
Chemical formula	C18H33NaO3
Molar mass	320.449 g·mol−1
Appearance	Pale white solid
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

As a surfactant, sodium ricinoleate is an irritant to human skin and mucous membranes, causing hypersensitivity responses. These are due to castor bean constituents, which can be removed in order to prepare it as a food-grade ingredient.[4]

Sodium ricinoleate was a constituent in toothpaste and was the 'SR' of Gibbs SR toothpaste, the first product to be advertised on British TV (in 1955).