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52444

Violaxanthin

Name: Violaxanthin
Brand: SIGMA

≥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

MDL number:

MFCD00075896

UNSPSC Code:

12352202

PubChem Substance ID:

329757838

NACRES:

NA.32

Beilstein/REAXYS Number:

101269

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Properties

Product Name

Violaxanthin, ≥90.0% (HPLC)

Quality Segment

100

assay

≥90.0% (HPLC)

form

solid

λ

in ethanol

UV absorption

λ: 438-442 nm A_max

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

Description

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.

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Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c