Cas no 126-29-4 (Violaxanthin)

Violaxanthin is a naturally occurring xanthophyll carotenoid found in various plants, algae, and photosynthetic organisms. It plays a critical role in the photoprotective mechanisms of the light-harvesting complex, particularly in the xanthophyll cycle, where it converts to zeaxanthin under high light stress. Violaxanthin is valued for its antioxidant properties, contributing to the neutralization of reactive oxygen species (ROS) and protection against oxidative damage. Its structural characteristics, including conjugated double bonds, make it a subject of interest in research related to photosynthesis, plant physiology, and nutraceuticals. The compound is also studied for potential applications in food additives, cosmetics, and health supplements due to its stability and bioactivity.
Violaxanthin structure
Violaxanthin structure
Product Name:Violaxanthin
CAS No:126-29-4
MF:C40H56O4
MW:600.870252609253
CID:181959
PubChem ID:329757838
Update Time:2025-10-31

Violaxanthin Chemical and Physical Properties

Names and Identifiers

    • b,b-Carotene-3,3'-diol,5,6:5',6'-diepoxy-5,5',6,6'-tetrahydro-, (3S,3'S,5R,5'R,6S,6'S)-
    • (1R,3S,6S)-6-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-18-[(1R,3S,6S)-3-hydroxy-1,5,5-trimethyl-7-oxabicyclo[4.1.0]heptan-6-yl]-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaenyl]-1,5,5-trimethyl-7-
    • trans-Violaxanthin
    • trans-Violaxanthin Discontinued See V634510
    • VIOLAXANTHIN
    • VIOLAXANTHIN(AS) (In Solution)
    • VIOLAXANTHIN(AS) (In Solution) PrintBack
    • VIOLAXANTHIN(SH)
    • (1R,3S,6S)-6-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-18-[(1R,3S,6S)-3-hydroxy-1,5,5-trimethyl-7-oxabicyclo[4.1.0]heptan-6-yl]-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaenyl]-1,5,5-trimethyl-7-oxabicyclo[4.1.0]heptan-3-ol
    • all-trans-Violaxanthil
    • all-trans-Violaxanthin
    • anti-violaxanthin
    • E161e
    • XAT
    • Zeaxanthin diepoxide
    • Zeaxanthin diepoxidl
    • (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
    • Violoxanthin
    • 5α,6α:5'α,6'α-Bisoxy-5,5',6,6'-tetrahydro-β,β-carotene-3β,3β'-diol
    • 5α,6α:5'α,6'α-Bisoxy-5,5',6,6'-tetrahydro-β,β-carotene-3β,3'β-diol
    • (3S,3'S,5R,5'R,6S,6'S,9E)-5,6:5',6'-Bisepoxy-5,5',6,6'-tetrahydro-β,β-carotene-3,3'-diol
    • (1R,3S,6S)-6-[18-[(1R,3S,6S)-3-hydroxy-1,5,5-trimethyl-7-oxabicyclo[4.1.0]hept-6-yl]-3,7,12,16-tetramethyl-octadeca-1,3,5,7,9,11,13,15,17-nonaenyl]-1,5,5-trimethyl-7-oxabicyclo[4.1.0]heptan-3-ol
    • (1S,4S,6R)-1-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-18-[(1S,4S,6R)-4-hydroxy-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl]-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaenyl]-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-4-ol
    • (1S,4S,6R)-1-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-18-[(1S,4S,6R)-4-hydroxy-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl]-3,7,12,16-tetramethyl-octadeca-1,3,5,7,9,11,13,15,17-nonaenyl]-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-4-ol
    • C08614
    • Q607883
    • (1R,3S,6S)-6-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-18-[(1S,4S,6R)-4-hydroxy-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl]-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaenyl]-1,5,5-trimethyl-7-oxabicyclo[4.1.0]heptan-3-ol
    • (3S,3'S,5R,5'R, 6S,6'S)-5,6:5',6'-Diepoxy-5,5',6,6'-tetrahydro-beta,beta-carotene-3,3'-diol
    • (1R,3S,6S)-6-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-18-[(1S,4S,6R)-4-hydroxy-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl]-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaen-1-yl]-1,5,5-trimethyl-7-oxabicyclo[4.1.0]heptan-3-ol
    • 5,6:5',6'-DIEPOXY-5,5',6,6'-TETRAHYDRO-.BETA.-CAROTENE-3,3'-DIOL
    • VIOLAXANTHIN, ALL-TRANS-
    • 51C926029A
    • CHEBI:35288
    • .BETA.,.BETA.-CAROTENE-3,3'-DIOL, 5,6:5',6'-DIEPOXY-5,5',6,6'-TETRAHYDRO-, (3S,3'S,5R,5'R,6S,6'S)-
    • ANTI,ANTI-VIOLAXANTHIN
    • Violaxanthin, >=90.0% (HPLC)
    • 126-29-4
    • VIOLAXANTHIN [MI]
    • (3S,3'S,5R,5'R,6S,6'S)-5,5',6,6'-tetrahydro-5,6:5',6'-diepoxy-beta,beta-carotene-3,3'-diol
    • (3S,3'S,5R,5'R, 6S,6'S)-5,6:5',6'-DIEPOXY-5,5',6,6'-TETRAHYDRO-.BETA.,.BETA.-CAROTENE-3,3'-DIOL
    • LMPR01070282
    • 5,6,5',6'-diepoxy-5,6,5',6'-tetrahydro-beta,beta-carotene-3,3'-diol
    • (3S,5R,6S,3'S,5'R,6'S)-5,6,5',6'-DIEPOXY-5,6,5',6'-TETRAHYDRO-BETA,BETA-CAROTENE-3,3'-DIOL
    • (3S,5R,6S,3'S,5'R,6'S)-5,6,5',6'-DIEPOXY-5,6,5',6'- TETRAHYDRO-BETA,BETA-CAROTENE-3,3'-DIOL
    • SZCBXWMUOPQSOX-WVJDLNGLSA-N
    • AKOS040763713
    • ALL-E-VIOLAXANTHIN
    • UNII-51C926029A
    • NS00070421
    • .BETA.-CAROTENE-3,3'-DIOL, 5,6:5',6'-DIEPOXY-5,5',6,6'-TETRAHYDRO-
    • beta,beta-Carotene-3,3'-diol, 5,6:5',6'-diepoxy-5,5',6,6'-tetrahydro-, (3S,3'S,5R,5'R,6S,6'S)-
    • C ORANGE 15
    • (3S,3'S,5R,5'R,6S,6'S)-5,6:5',6'-diepoxy-5,5',6,6'-tetrahydro-beta,beta-carotene-3,3'-diol
    • 5,6:5',6'-Diepoxy-5,5',6,6'-tetrahydro-beta-carotene-3,3'-diol
    • 09958A8F-4AFE-43DB-9034-C562F62D8ABD
    • 1ST159340
    • 5-(TRIFLUOROMETHYL)PYRIDIN-2-YL]ACETONITRILE
    • SCHEMBL97720
    • DB03460
    • E 161e
    • DTXSID901016934
    • VIOLAXANTHIN (E 161E)
    • HY-N9625
    • CS-0202315
    • CHEBI:27295
    • DTXCID001475117
    • BETA-CAROTENE-3,3'-DIOL, 5,6:5',6'-DIEPOXY-5,5',6,6'-TETRAHYDRO-
    • (1R,3S,6S)-6-((1E,3E,5E,7E,9E,11E,13E,15E,17E)-18-((1S,4S,6R)-4-hydroxy-2,2,6-trimethyl-7-oxabicyclo(4.1.0)heptan-1-yl)-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaenyl)-1,5,5-trimethyl-7-oxabicyclo(4.1.0)heptan-3-ol
    • Violaxanthin
    • 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
    • SMILES: O1[C@]2(C)C[C@H](CC(C)(C)[C@]12/C=C/C(=C/C=C/C(=C/C=C/C=C(\C)/C=C/C=C(\C)/C=C/[C@]12C(C)(C)C[C@@H](C[C@@]1(C)O2)O)/C)/C)O

Computed Properties

  • Exact Mass: 600.41800
  • Monoisotopic Mass: 600.418
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 2
  • Hydrogen Bond Acceptor Count: 4
  • Heavy Atom Count: 44
  • Rotatable Bond Count: 10
  • Complexity: 1270
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 6
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 9
  • Undefined Bond Stereocenter Count: 0
  • Surface Charge: 0
  • Tautomer Count: nothing
  • XLogP3: 9.8
  • Topological Polar Surface Area: 65.5A^2

Experimental Properties

  • Density: 0.9826 (rough estimate)
  • Melting Point: 200°
  • Boiling Point: 570.8°C (rough estimate)
  • Flash Point: 380.7°C
  • Refractive Index: 1.4760 (estimate)
  • PSA: 65.52000
  • LogP: 8.96980
  • Specific Rotation: 20Cd +35° (c = 0.08 in chloroform)
  • Solubility: Soluble in ethanol and ether, insoluble in petroleum ether.

Violaxanthin Security Information

  • Hazardous Material transportation number:NONH for all modes of transport
  • WGK Germany:3
  • Storage Condition:?20°C

Violaxanthin Pricemore >>

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Violaxanthin Related Literature

Additional information on Violaxanthin

Professional Introduction to Violaxanthin (CAS No. 126-29-4)

Violaxanthin, with the chemical formula C40H56O4, is a carotenoid pigment that is naturally found in various plants, particularly in the leaves of Viola species. This compound is well-known for its vibrant yellow-green color and has garnered significant attention in the fields of nutrition, cosmetics, and pharmaceutical research due to its remarkable biological properties. The CAS number CAS No. 126-29-4 uniquely identifies this molecule and distinguishes it from other carotenoids, underscoring its importance in scientific and industrial applications.

The structural configuration of violaxanthin is characterized by a conjugated system of double bonds, which contributes to its strong antioxidant activity. This feature has been extensively studied in recent years, particularly in the context of cellular protection against oxidative stress. Research has demonstrated that violaxanthin can scavenge free radicals and inhibit the production of reactive oxygen species (ROS), thereby mitigating damage to cellular components such as lipids, proteins, and DNA. These findings have fueled interest in violaxanthin as a potential therapeutic agent for various oxidative stress-related diseases.

In addition to its antioxidant properties, violaxanthin has been shown to exhibit photoprotective effects. This is attributed to its ability to absorb harmful ultraviolet (UV) radiation and convert it into heat, thereby protecting living tissues from UV-induced damage. Recent studies have highlighted the role of violaxanthin in maintaining skin health by reducing erythema and preventing photoaging. These benefits have led to its incorporation into cosmetic formulations aimed at protecting against environmental stressors and promoting skin vitality.

The biosynthesis of violaxanthin involves a complex pathway known as the xanthophyll cycle, which is crucial for adapting to changing light conditions. This cycle begins with the conversion of lutein to zeaxanthin, followed by the addition of an oxygen atom to form violaxanthin. The enzyme responsible for this transformation is zeaxanthin epoxidase (ZEP), which plays a key role in regulating the levels of these carotenoids within plant cells. Understanding this pathway has implications for agricultural practices aimed at enhancing the nutritional content of crops rich in carotenoids.

Recent advancements in analytical techniques have improved our ability to quantify violaxanthin in biological samples. High-performance liquid chromatography (HPLC) coupled with mass spectrometry (MS) has become the gold standard for detecting and measuring violaxanthin levels in tissues and plasma. These methods have enabled researchers to investigate the pharmacokinetics and metabolic pathways of violaxanthin, providing valuable insights into its potential therapeutic applications. For instance, studies have shown that violaxanthin can be efficiently absorbed after oral administration and distributed throughout the body, suggesting its suitability for systemic treatments.

The therapeutic potential of violaxanthin extends beyond antioxidant and photoprotective effects. Emerging research has explored its role in modulating inflammatory responses and enhancing immune function. In preclinical studies, violaxanthin has been found to inhibit the production of pro-inflammatory cytokines such as tumor necrosis factor-alpha (TNF-α) and interleukin-6 (IL-6). These findings suggest that violaxanthin may have anti-inflammatory properties that could be beneficial in managing chronic inflammatory diseases such as rheumatoid arthritis and inflammatory bowel disease.

The cosmetic industry has also embraced violaxanthin due to its skin-beneficial properties. Its ability to protect against UV-induced damage makes it an ideal ingredient for sunscreens and anti-aging creams. Furthermore, violaxanthin's antioxidant activity helps combat free radical damage caused by environmental pollutants, contributing to overall skin health. Several clinical trials have demonstrated that topical formulations containing violaxanthin can improve skin texture, reduce wrinkles, and enhance collagen production. These results have bolstered consumer interest in products enriched with this natural pigment.

The extraction and purification of violaxanthin from natural sources remain challenging due to its limited availability in plants. However, advancements in biotechnology have enabled the development of microbial fermentation methods for producing carotenoids on an industrial scale. Genetically modified microorganisms such as yeast and bacteria have been engineered to efficiently synthesize violaxanthin, offering a sustainable alternative to plant-based extraction. These innovations are expected to increase the availability of violaxanthin for research and commercial applications.

The future prospects of violaxanthin research are promising, with ongoing studies exploring its potential applications in neuroprotection, cancer prevention, and metabolic disorders. For instance, preliminary research suggests that violaxanthin may help protect against neurodegenerative diseases such as Alzheimer's by reducing oxidative stress and inflammation in brain cells. Similarly, its anti-cancer properties are being investigated through cell culture and animal models, with early results indicating that violaxanthin can induce apoptosis in cancerous cells while sparing healthy cells.

In conclusion, Violaxanthin (CAS No. 126-29-4) is a multifaceted carotenoid with significant potential across multiple industries. Its antioxidant, photoprotective, anti-inflammatory, and immunomodulatory properties make it a valuable compound for nutritional supplements, cosmetic formulations, and pharmaceutical applications. As research continues to uncover new therapeutic benefits of violaxanthin, its role in promoting health and wellness is likely to expand further.

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