Bixin: Difference between revisions

Bixin^[1]
Names
	IUPAC name (2E,4E,6E,8E,10E,12E,14E,16Z,18E)-20-Methoxy-4,8,13,17-tetramethyl-20-oxoicosa-2,4,6,8,10,12,14,16,18-nonaenoic acid
	Other names cis-Bixin; α-Bixin; 9-cis-6,6'-Diapo-ψ,ψ-carotenedioic acid, 6-methyl ester
Identifiers
CAS Number	6983-79-5 ; 39937-23-0 (trans) ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:3136;
ChEMBL	ChEMBL1172615 ;
ChemSpider	4444638 ;
ECHA InfoCard	100.027.499
PubChem CID	5281226;
UNII	9L7T4VB66G ; 6JH6LEZ7HY (trans) ;
CompTox Dashboard (EPA)	DTXSID1024629 ;
	InChI InChI=1S/C25H30O4/c1-20(12-8-14-22(3)16-18-24(26)27)10-6-7-11-21(2)13-9-15-23(4)17-19-25(28)29-5/h6-19H,1-5H3,(H,26,27)/b7-6+,12-8+,13-9+,18-16+,19-17+,20-10+,21-11+,22-14+,23-15+ Key: RAFGELQLHMBRHD-IFNPSABLSA-N ; InChI=1/C25H30O4/c1-20(12-8-14-22(3)16-18-24(26)27)10-6-7-11-21(2)13-9-15-23(4)17-19-25(28)29-5/h6-19H,1-5H3,(H,26,27)/b7-6+,12-8+,13-9+,18-16+,19-17+,20-10+,21-11+,22-14+,23-15- Key: RAFGELQLHMBRHD-SLEZCNMEBU;
	SMILES O=C(O)\C=C\C(=C\C=C\C(=C\C=C\C=C(\C=C\C=C(/C=C/C(=O)OC)C)C)C)C;
Properties
Chemical formula	C25H30O4
Molar mass	394.511 g·mol−1
Appearance	Orange crystals
Melting point	198 °C (cis-isomer) ; 217 °C (trans-isomer)
Solubility in water	Insoluble
Hazards
NFPA 704 (fire diamond)	1 1 0
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

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Bixin is an apocarotenoid found in the seeds of the achiote tree (Bixa orellana)^[2] from which it derives its name. It is commonly extracted from the seeds to form annatto, a natural food coloring, containing about 5% pigments, of which 70–80% are bixin.^[3]

Applications

Bixin is one of the colorants used in the snack Cheetos.

Several thousand tons are harvested annually.^[4]

Chemical properties

Bixin is unstable. It isomerizes into trans-bixin (β-bixin), the double-bond isomer.^[1]

Chemical structure of trans-bixin

Bixin is soluble in fats and alcohols but insoluble in water. Upon exposure to alkali, the methyl ester is hydrolyzed to produce the dicarboxylic acid norbixin, a water-soluble derivative.

Chemical structure of norbixin

References

^ ^a ^b Merck Index, 11th Edition, 1320
^ Bouvier, Florence; Dogbo, Odette; Camara, Bilal (2003). "Biosynthesis of the Food and Cosmetic Plant Pigment Bixin (Annatto)". Science. 300 (5628): 2089–2091. Bibcode:2003Sci...300.2089B. doi:10.1126/science.1085162. ISSN 0036-8075. JSTOR 3834418. PMID 12829782. S2CID 560600.
^ Executive Summary Bixin Archived July 21, 2011, at the Wayback Machine, National Toxicology Program
^ Stringheta, Paulo C.; Silva, Pollyanna I.; Costa, André G.V. (2018). "Annatto/Urucum— Bixa orellana". Exotic Fruits. pp. 23–30. doi:10.1016/B978-0-12-803138-4.00006-X. ISBN 9780128031384.

[Merck-1] Merck Index, 11th Edition, 1320

[2] Bouvier, Florence; Dogbo, Odette; Camara, Bilal (2003). "Biosynthesis of the Food and Cosmetic Plant Pigment Bixin (Annatto)". Science. 300 (5628): 2089–2091. Bibcode:2003Sci...300.2089B. doi:10.1126/science.1085162. ISSN 0036-8075. JSTOR 3834418. PMID 12829782. S2CID 560600.

[3] Executive Summary Bixin Archived July 21, 2011, at the Wayback Machine, National Toxicology Program

[4] Stringheta, Paulo C.; Silva, Pollyanna I.; Costa, André G.V. (2018). "Annatto/Urucum— Bixa orellana". Exotic Fruits. pp. 23–30. doi:10.1016/B978-0-12-803138-4.00006-X. ISBN 9780128031384.

[1]

[2]

[3]

[4]

@@ Line 3: / Line 3: @@
 | verifiedrevid = 459980646
 | Reference = <ref name="Merck">''[[Merck Index]]'', 11th Edition, '''1320'''</ref>
-| ImageFile = Bixin.png
+| ImageFile = Bixina.svg
 | ImageSize = 300
 | ImageName = Skeletal formula
+| IUPACName = (2''E'',4''E'',6''E'',8''E'',10''E'',12''E'',14''E'',16''Z'',18''E'')-20-Methoxy-4,8,13,17-tetramethyl-20-oxoicosa-2,4,6,8,10,12,14,16,18-nonaenoic acid
-| ImageFile1 = Cis-bixin-3D-balls-(rotated).png
-| ImageSize1 = 310
-| ImageName1 = Ball-and-stick model
-| IUPACName = (2''E'',4''E'',6''E'',8''E'',10''E'',12''E'',14''E'',16''Z'',18''E'')-20-methoxy-4,8,13,17-tetramethyl-20-oxoicosa-2,4,6,8,10,12,14,16,18-nonaenoic acid
 | OtherNames = ''cis''-Bixin; α-Bixin; 9-''cis''-6,6'-Diapo-ψ,ψ-carotenedioic acid, 6-methyl ester
 | Section1 = {{Chembox Identifiers
 | ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
 | ChemSpiderID = 4444638
+| ChEBI = 3136
-| ChEMBL 1172615
+| ChEMBL_Ref = {{ebicite|changed|EBI}}
+| ChEMBL = 1172615
 | InChI = 1/C25H30O4/c1-20(12-8-14-22(3)16-18-24(26)27)10-6-7-11-21(2)13-9-15-23(4)17-19-25(28)29-5/h6-19H,1-5H3,(H,26,27)/b7-6+,12-8+,13-9+,18-16+,19-17+,20-10+,21-11+,22-14+,23-15-
 | InChIKey = RAFGELQLHMBRHD-SLEZCNMEBU
-| CASNo_Ref = {{cascite|changed|??}}
+| CASNo_Ref = {{cascite|correct|CAS}}
 | CASNo = 6983-79-5
+| CASNo2_Ref = {{cascite|correct|CAS}}
-|  CASOther = <br>39937-23-0 (''trans''-Bixin)
+| CASNo2 = 39937-23-0
+| CASNo2_Comment = (''trans'')
 | StdInChI_Ref = {{stdinchicite|correct|chemspider}}
 | StdInChI = 1S/C25H30O4/c1-20(12-8-14-22(3)16-18-24(26)27)10-6-7-11-21(2)13-9-15-23(4)17-19-25(28)29-5/h6-19H,1-5H3,(H,26,27)/b7-6+,12-8+,13-9+,18-16+,19-17+,20-10+,21-11+,22-14+,23-15+
@@ Line 27: / Line 28: @@
 | UNII_Ref = {{fdacite|correct|FDA}}
 | UNII = 9L7T4VB66G
+| UNII1_Ref = {{fdacite|correct|FDA}}
+| UNII1 = 6JH6LEZ7HY
+| UNII1_Comment = (''trans'')
 | SMILES = O=C(O)\C=C\C(=C\C=C\C(=C\C=C\C=C(\C=C\C=C(/C=C/C(=O)OC)C)C)C)C
 }}
@@ Line 33: / Line 37: @@
 | Appearance = Orange crystals
 | Density =
-| MeltingPt =
+| MeltingPt = 198 °C (cis-isomer) <br /> 217 °C (trans-isomer)
 | BoilingPt =
 | Solubility = Insoluble}}
 | Section3 = {{Chembox Hazards
+|  NFPA-H = 1
+|  NFPA-F = 1
+|  NFPA-R = 0
 | MainHazards =
 | FlashPt =
-| Autoignition = }}
+| AutoignitionPt = }}
 }}
-'''Bixin''' is an [[apocarotenoid]] found in [[annatto]], a natural [[food coloring]] obtained from the seeds of the [[Bixa orellana|achiote tree]] (''Bixa orellana'').  Annatto seeds contain about 5% pigments, which consist of 70-80% bixin.<ref>[http://ntp-server.niehs.nih.gov/?objectid=F59ACAC5-F1F6-975E-7C563568F5F7351B#selection Executive Summary Bixin], National Toxicology Program</ref>
+'''Bixin''' is an [[apocarotenoid]] found in the seeds of the [[Bixa orellana|achiote tree]] (''Bixa orellana'')<ref>{{Cite journal|last1=Bouvier|first1=Florence|last2=Dogbo|first2=Odette|last3=Camara|first3=Bilal|date=2003|title=Biosynthesis of the Food and Cosmetic Plant Pigment Bixin (Annatto)|url=https://www.jstor.org/stable/3834418|journal=Science|volume=300|issue=5628|pages=2089–2091|doi=10.1126/science.1085162 |jstor=3834418 |pmid=12829782 |bibcode=2003Sci...300.2089B |s2cid=560600 |issn=0036-8075}}</ref> from which it derives its name. It is commonly extracted from the seeds to form [[annatto]], a natural [[food coloring]], containing about 5% pigments, of which 70–80% are bixin.<ref>[https://ntp.niehs.nih.gov/ntp/htdocs/chem_background/exsumpdf/bixin_508.pdf Executive Summary Bixin] {{webarchive |url=https://web.archive.org/web/20110721055506/http://ntp-server.niehs.nih.gov/?objectid=F59ACAC5-F1F6-975E-7C563568F5F7351B#selection |date=July 21, 2011 }}, National Toxicology Program</ref>
+==Applications==
-Bixin is chemically unstable when isolated and converts via [[isomerization]] into ''trans''-bixin (β-bixin), the [[Cis-trans isomerism|double-bond isomer]].<ref name="Merck"/>
+:[[image:Bixa orellana fruit open.jpg|thumb|center|Red seeds of the achiote tree]]
+:[[file:CheetosCrop.jpg|thumb|Bixin is one of the colorants used in the snack Cheetos.]]
+Several thousand tons are harvested annually.<ref>{{cite book |doi=10.1016/B978-0-12-803138-4.00006-X|chapter=Annatto/Urucum— Bixa orellana |title=Exotic Fruits |year=2018 |last1=Stringheta |first1=Paulo C. |last2=Silva |first2=Pollyanna I. |last3=Costa |first3=André G.V. |pages=23–30 |isbn=9780128031384 }}</ref>
+==Chemical properties==
-Bixin is soluble in fats but insoluble in water. Upon exposure to [[alkali]], the [[methyl]] [[ester]] is [[hydrolysis|hydrolyzed]] to produce the [[dicarboxylic acid]] '''norbixin''', a water-soluble derivative.
+Bixin is unstable. It [[isomerization|isomerizes]] into ''trans''-bixin (β-bixin), the [[Cis-trans isomerism|double-bond isomer]].<ref name="Merck"/>
+:[[File:Trans-bixin.png|thumb|center|320px|Chemical structure of ''trans''-bixin]]
+Bixin is soluble in fats and [[alcohols]] but insoluble in water. Upon exposure to [[alkali]], the [[methyl]] [[ester]] is [[hydrolysis|hydrolyzed]] to produce the [[dicarboxylic acid]] '''norbixin''', a water-soluble derivative.
-:[[File:Trans-bixin.png|thumb|left|320px|Chemical structure of ''trans''-bixin]]
-:[[File:Trans-bixin-3D-balls-(rotated).png|thumb|left|320px|Ball-and-stick model of ''trans''-bixin]]
+:[[File:norbixin structure.png|thumb|center|300px|Chemical structure of norbixin]]{{clear-left}}
-:[[File:norbixin structure.png|thumb|left|300px|Chemical structure of norbixin]]{{clear-left}}
 ==References==
@@ Line 58: / Line 69: @@
 [[Category:Apocarotenoids]]
+[[Category:E-number additives]]
-[[ca:Bixina]]
-[[de:Bixin]]
-[[es:Bixina]]
-[[fa:بیکسین]]
-[[it:Bixina]]
-[[lt:Biksinas]]
-[[nl:Bixine]]
-[[ja:ビキシン]]
-[[pl:Biksyna]]
-[[pt:Bixina]]

v t e Carotenoids
Carotenes (C₄₀)	α-Carotene β-Carotene γ-Carotene δ-Carotene ε-Carotene ζ-Carotene Lycopene Neurosporene Phytoene Phytofluene Torulene Lycopersene
Xanthophylls (C₄₀)	Antheraxanthin Astaxanthin Canthaxanthin Citranaxanthin Cryptoxanthin Diadinoxanthin Diatoxanthin Dinoxanthin Echinenone Flavoxanthin Fucoxanthin Lutein Neoxanthin Rhodoxanthin Rubixanthin Violaxanthin Zeaxanthin Zeinoxanthin
Apocarotenoids (C_<40)	Abscisic acid Apocarotenal Bixin Crocetin Food orange 7 Ionones Peridinin
Vitamin A retinoids (C₂₀)	Retinal Retinoic acid Retinol
Retinoid drugs	Acitretin Alitretinoin Bexarotene Etretinate Fenretinide Isotretinoin Tazarotene Temarotene Tretinoin Zuretinol acetate