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52444

Sigma-Aldrich

Violaxanthin

≥90.0% (HPLC), solid

Synonym(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

Empirical Formula (Hill Notation):
C40H56O4
CAS Number:
126-29-4
Molecular Weight:
600.87
Beilstein:
101269
UNSPSC Code:
12352202
PubChem Substance ID:
329757838
NACRES:
NA.32

product name

Violaxanthin, ≥90.0% (HPLC)

Assay

≥90.0% (HPLC)

form

solid

λ

in ethanol

UV absorption

λ: 438-442 nm Amax

storage temp.

−20°C

SMILES string

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

InChI key

SZCBXWMUOPQSOX-WVJDLNGLSA-N

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General description

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.

Biochem/physiol Actions

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.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Formation and breakdown of ABA.
Cutler AJ and Krochko JE
Trends in Plant Science, 4, 472-478 (1999)
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
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
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
K K Niyogi et al.
The Plant cell, 10(7), 1121-1134 (1998-07-21)
A conserved regulatory mechanism protects plants against the potentially damaging effects of excessive light. Nearly all photosynthetic eukaryotes are able to dissipate excess absorbed light energy in a process that involves xanthophyll pigments. To dissect the role of xanthophylls in
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