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{{chembox
{{chembox
| verifiedrevid =
| verifiedrevid =
| ImageFile=Ricinoleic acid.svg
| ImageFile=Sodium ricinoleate.svg
| ImageSize=250px
| ImageSize=250px
| IUPACName=Sodium (''R'',''Z'')-12-hydroxyoctadec-9-enoate
| PIN=Sodium (9''Z'',12''R'')-12-hydroxyoctadec-9-enoate
| OtherNames=Ricinoleic acid sodium salt
| OtherNames=Ricinoleic acid sodium salt
| Section1 = {{Chembox Identifiers
|Section1={{Chembox Identifiers
| CASNo = 5323-95-5
| CASNo = 5323-95-5
| CASNo_Ref = {{cascite|correct|}}
| CASNo_Ref = {{cascite|correct|}}
| ChemSpiderID = 17215848
⚫
| PubChem =
| EC_number = 226-191-2
⚫
| SMILES = O[C@H](CCCCCC)C/C=C\CCCCCCCC([O-])=O.[Na+]
| RTECS = VJ3500000
⚫
}}
| UNII_Ref = {{fdacite|correct|FDA}}
⚫
| Section2={{Chembox Properties
| UNII = OOO64813BX
⚫
| C=18|H=33|Na=1|O=3
⚫
| PubChem = 23687338
⚫
| Appearance= Pale white solid
⚫
| SMILES = O[C@H](CCCCCC)C/C=C\CCCCCCCC([O-])=O.[Na+]
⚫
| Density=
| StdInChI = 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
| MeltingPtCL=
| StdInChIKey = IJRHDFLHUATAOS-DPMBMXLASA-M
| MeltingPtCH=

⚫
| BoilingPt=
⚫
}}
⚫
| Solubility=
⚫
|Section2={{Chembox Properties
⚫
}}
⚫
| C=18 | H=33 | Na=1 | O=3
| Section3=
⚫
| Appearance= Pale white solid
⚫
| Density=
| MeltingPtC=
⚫
| BoilingPt=
⚫
| Solubility=
⚫
}}
}}
}}


'''Sodium ricinoleate''' is the [[sodium]] [[salt (chemistry)|salt]] of [[ricinoleic acid]], the principle [[fatty acid]] derived from [[castor oil]].{{sfnp|Dunn|2010|p=187}} It is used in making [[soap]], where its molecular structure causes it to lather more easily than comparable sodium soaps derived from fatty acids.{{sfnp|Dunn|2010|p=187}} It is a [[bactericide]].{{sfnp|Ann Surg|1932}} It exhibits several [[Lipid polymorphism|polymorphic structural phases]].{{sfnp|Liquid Crystals|1994}}
'''Sodium ricinoleate''' is the [[sodium]] [[salt (chemistry)|salt]] of [[ricinoleic acid]], the principal [[fatty acid]] derived from [[castor oil]].{{sfnp|Dunn|2010|p=187}} It is used in making [[soap]], where its molecular structure causes it to lather more easily than comparable sodium soaps derived from fatty acids.{{sfnp|Dunn|2010|p=187}} It is a [[bactericide]].{{sfnp|Ann Surg|1932}} It exhibits several [[Lipid polymorphism|polymorphic structural phases]].{{sfnp|Liquid Crystals|1994}}


As a [[surfactant]], sodium ricinoleate is an irritant to human [[skin]] and [[mucus membrane]]s, causing [[hypersensitivity]] responses. These are due to [[castor bean]] constituents, which can be removed in order to prepare it as a food-grade ingredient.{{sfnp|Food Chem Toxicol|2006}}
As a [[surfactant]], sodium ricinoleate is an irritant to human [[skin]] and [[mucous membrane]]s, causing [[hypersensitivity]] responses. These are due to [[castor bean]] constituents, which can be removed in order to prepare it as a food-grade ingredient.{{sfnp|Food Chem Toxicol|2006}}


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

== References ==
<references />
<references />


== Citations ==
== Citations ==
{{refbegin}}
{{refbegin}}
* {{cite book|title=Scientific Soapmaking: The Chemistry of the Cold Process|first=Kevin M.|last=Dunn|year=2010|publisher=Clavicula Press|url=http://books.google.co.uk/books?id=DL0d6AoATfwC|accessdate=5 February 2013|ref=harv}}
* {{cite book|title=Scientific Soapmaking: The Chemistry of the Cold Process|first=Kevin M.|last=Dunn|year=2010|publisher=Clavicula Press|url=https://books.google.com/books?id=DL0d6AoATfwC|access-date=5 February 2013|isbn=9781935652090}}
* {{cite journal|title=Sodium Ricinoleate: Its Possible Value in the Prevention and Treatment of Peritonitis|journal=[[Annals of Surgery]]|first=Sam F.|last=Seeley|date=September 1932|volume=96|issue=3|pages=350–8|pmc=1391690|url=http://www.ncbi.nlm.nih.gov/pmc/articles/PMC1391690/|accessdate=5 February 2013|ref={{SfnRef|Ann Surg|1932}}|doi=10.1097/00000658-193209000-00004}}
* {{cite journal|title=Sodium Ricinoleate: Its Possible Value in the Prevention and Treatment of Peritonitis|journal=[[Annals of Surgery]]|first=Sam F.|last=Seeley|date=September 1932|volume=96|issue=3|pages=350–8|pmc=1391690|ref={{SfnRef|Ann Surg|1932}}|doi=10.1097/00000658-193209000-00004|pmid=17866830}}
* {{cite journal|title=Toxicology and pharmacology of sodium ricinoleate|journal=[[Food and Chemical Toxicology]]|date=Oct 2006|volume=44|issue=10|pages=1689–98|last1=Burdock|first1=GA|last2=Carabin|first2=IG|last3=Griffiths|first3=JC|doi=10.1016/j.fct.2006.05.007|accessdate=5 February 2013|ref={{SfnRef|Food Chem Toxicol|2006}}|pmid=16831502}}
* {{cite journal|title=Toxicology and pharmacology of sodium ricinoleate|journal=[[Food and Chemical Toxicology]]|date=Oct 2006|volume=44|issue=10|pages=1689–98|last1=Burdock|first1=GA|last2=Carabin|first2=IG|last3=Griffiths|first3=JC|doi=10.1016/j.fct.2006.05.007|ref={{SfnRef|Food Chem Toxicol|2006}}|pmid=16831502}}
* {{cite journal|journal=Liquid Crystals|volume=17|issue=5|year=1994|title=The thermotropic liquid crystals formed by anhydrous sodium ricinoleate|doi=10.1080/02678299408037333|first1=K.S.|last1=Narayana|first2=Neeta|last2=Shindeab|first3=Gordon J. T.|last3=Tiddy|first4=Michael C.|last4=Holmes|pages= 617–28|url=http://www.tandfonline.com/doi/abs/10.1080/02678299408037333|accessdate=5 February 2013|ref={{SfnRef|Liquid Crystals|1994}}}}
* {{cite journal|journal=Liquid Crystals|volume=17|issue=5|year=1994|title=The thermotropic liquid crystals formed by anhydrous sodium ricinoleate|doi=10.1080/02678299408037333|first1=K.S.|last1=Narayana|first2=Neeta|last2=Shindeab|first3=Gordon J. T.|last3=Tiddy|first4=Michael C.|last4=Holmes|pages= 617–28|ref={{SfnRef|Liquid Crystals|1994}}}}
{{refend}}
{{refend}}


[[Category:Sodium compounds]]
[[Category:Organic sodium salts]]


{{organic-compound-stub}}

Latest revision as of 17:30, 22 January 2023

Sodium ricinoleate
Names
Preferred IUPAC name
Sodium (9Z,12R)-12-hydroxyoctadec-9-enoate
Other names
Ricinoleic acid sodium salt
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.023.811 Edit this at Wikidata
EC Number
  • 226-191-2
RTECS number
  • VJ3500000
UNII
  • 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
  • O[C@H](CCCCCC)C/C=C\CCCCCCCC([O-])=O.[Na+]
Properties
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).

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]

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).

References

[edit]
  1. ^ a b Dunn (2010), p. 187.
  2. ^ Ann Surg (1932).
  3. ^ Liquid Crystals (1994).
  4. ^ Food Chem Toxicol (2006).

Citations

[edit]
  • Dunn, Kevin M. (2010). Scientific Soapmaking: The Chemistry of the Cold Process. Clavicula Press. ISBN 9781935652090. Retrieved 5 February 2013.
  • Seeley, Sam F. (September 1932). "Sodium Ricinoleate: Its Possible Value in the Prevention and Treatment of Peritonitis". Annals of Surgery. 96 (3): 350–8. doi:10.1097/00000658-193209000-00004. PMC 1391690. PMID 17866830.
  • Burdock, GA; Carabin, IG; Griffiths, JC (Oct 2006). "Toxicology and pharmacology of sodium ricinoleate". Food and Chemical Toxicology. 44 (10): 1689–98. doi:10.1016/j.fct.2006.05.007. PMID 16831502.
  • Narayana, K.S.; Shindeab, Neeta; Tiddy, Gordon J. T.; Holmes, Michael C. (1994). "The thermotropic liquid crystals formed by anhydrous sodium ricinoleate". Liquid Crystals. 17 (5): 617–28. doi:10.1080/02678299408037333.
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