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52444

Sigma-Aldrich

Violaxanthin

≥90.0% (HPLC), solid

Synonyme(s) :

(3S,3′S,5R,5′R,6S,6′S)-5,6:5′,6′-Diepoxy-5,5′,6,6′-tetrahydro-β,β-carotene-3,3′-diol

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About This Item

Formule empirique (notation de Hill):
C40H56O4
Numéro CAS:
126-29-4
Poids moléculaire :
600.87
Numéro Beilstein :
101269
Code UNSPSC :
12352202
ID de substance PubChem :
329757838
Nomenclature NACRES :
NA.32

product name

Violaxanthin, ≥90.0% (HPLC)

Pureté

≥90.0% (HPLC)

Forme

solid

λ

in ethanol

Absorption UV

λ: 438-442 nm Amax

Température de stockage

−20°C

Chaîne SMILES 

CC(/C=C/[C@@]12[C@](C)(O2)C[C@@H](O)CC1(C)C)=C\C=C\C(C)=C\C=C\C=C(C)\C=C\C=C(\C=C\[C@]34C(C)(C)C[C@H](O)C[C@]3(O4)C)C

InChI

1S/C40H56O4/c1-29(17-13-19-31(3)21-23-39-35(5,6)25-33(41)27-37(39,9)43-39)15-11-12-16-30(2)18-14-20-32(4)22-24-40-36(7,8)26-34(42)28-38(40,10)44-40/h11-24,33-34,41-42H,25-28H2,1-10H3/b12-11+,17-13+,18-14+,23-21+,24-22+,29-15+,30-16+,31-19+,32-20+/t33-,34-,37+,38+,39-,40-/m0/s1

Clé InChI

SZCBXWMUOPQSOX-WVJDLNGLSA-N

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Description générale

Violaxanthin is an epoxidized carotenoid obtained from plants. It is an orange-colored natural xanthophyll pigment.

Application

Violaxanthin has been used as a standard/control in high-pressure liquid chromatography (HPLC) analysis of pigment extracts to confirm the high-level astaxanthin accumulation suspected from the visual phenotype of Nt-AXT plants.

Actions biochimiques/physiologiques

Violaxanthin is a carotene epoxide that is a precursor to capsanthin. It is one of three xanthophylls involved in the evolution of plastids of green plants (oxygen evolution) and participating in photo-induced interconversions known as the violaxanthin cycle. The cleavage of 9-cis-epoxycarotenoids (violaxanthin) to xanthoxin is the key regulatory step of abscisic acid biosynthesis.
Violaxanthin is a powerful antioxidant and a vital precursor to important compounds like fucoxanthin and β-damascenone. It is a non-photochemical fluorescence quenching structural component of the xanthophyll cycle that shields the photosynthetic system from excessive light. The 2,2′-azinobis-3-ethylbenzothiazoline-6-sulfonic acid (ABTS+) radical scavenging action of violaxanthin extracted from water spinach/water morning glory is strong, and it also inhibits lipid peroxidation and red blood cell hemolysis. Hence, it has the potential to be used in a wide range of medicinal and health products.

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Certificats d'analyse (COA)

Recherchez un Certificats d'analyse (COA) en saisissant le numéro de lot du produit. Les numéros de lot figurent sur l'étiquette du produit après les mots "Lot" ou "Batch".

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T Kinoshita et al.
Nature, 414(6864), 656-660 (2001-12-12)
The stomatal pores of higher plants allow for gaseous exchange into and out of leaves. Situated in the epidermis, they are surrounded by a pair of guard cells which control their opening in response to many environmental stimuli, including blue
Feifei Wang et al.
Marine drugs, 16(6) (2018-06-03)
Violaxanthin is a major xanthophyll pigment in the microalga Eustigmatos cf. polyphem, but the amount produced after propagation can vary depending upon culture conditions. In this study, the effects of cultivation time, nitrogen concentration, light intensity, and culture mode on
M Havaux et al.
Proceedings of the National Academy of Sciences of the United States of America, 96(15), 8762-8767 (1999-07-21)
When light energy absorbed by plants becomes excessive relative to the capacity of photosynthesis, the xanthophyll violaxanthin is reversibly deepoxidized to zeaxanthin (violaxanthin cycle). The protective function of this phenomenon was investigated in a mutant of Arabidopsis thaliana, npq1, that
Formation and breakdown of ABA.
Cutler AJ and Krochko JE
Trends in Plant Science, 4, 472-478 (1999)
The spectral determination of chlorophylls a and b, as well as total carotenoids, using various solvents with spectrophotometers of different resolution.
Wellburn, A.R.
Journal of Plant Physiology, 144, 307-313 (1994)
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