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54764

Sigma-Aldrich

Neoxanthin

≥90% (HPLC)

Synonym(s):

(3S,3′S,5R,5′R,6R,6′S,9′-cis)-6,7-Didehydro-5′,6′-epoxy-5′,6′-dihydro-β,β-carotene-3,3′,5(6H)-triol, 9′-cis-Neoxanthin

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About This Item

Empirical Formula (Hill Notation):
C40H56O4
CAS Number:
14660-91-4
Molecular Weight:
600.87
UNSPSC Code:
12352202
NACRES:
NA.32

Assay

≥90% (HPLC)

form

solid

λ

in ethanol

UV absorption

λ: 435-439 nm Amax

storage temp.

−20°C

SMILES string

C/C(C([H])=[C@]=C1[C@](C)(O)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@@]2(O3)[C@@]3(C)C[C@@H](O)CC2(C)C)C

InChI

1S/C40H56O4/c1-29(17-13-19-31(3)21-22-35-36(5,6)25-33(41)27-38(35,9)43)15-11-12-16-30(2)18-14-20-32(4)23-24-40-37(7,8)26-34(42)28-39(40,10)44-40/h11-21,23-24,33-34,41-43H,25-28H2,1-10H3/b12-11+,17-13+,18-14+,24-23+,29-15+,30-16+,31-19+,32-20+/t22?,33-,34-,38+,39+,40-/m0/s1

InChI key

PGYAYSRVSAJXTE-CLONMANBSA-N

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Application

Neoxanthin has been used as a reference standard to determine the phenolic content and antioxidant activity of Phaeodactylum tricornutum extracts by high-performance liquid chromatography (HPLC).

Biochem/physiol Actions

Neoxanthin is an allenic xanthophyll and one of the major carotenoids found in plants such as spinach and barley leaves. A trace amount of this pigment is also found in olive oil. Neoxanthin exists as two geometric isomers such as trans-neoxanthin and 9′-cis-neoxanthin. It acts as a precursor of abscisic acid. It plays a role in photoprotection by providing general antioxidant activity. Neoxanthin exhibits apoptotic and anti-proliferative effects.

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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Kranthi K Chebrolu et al.
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences, 1001, 41-48 (2015-08-11)
A high-throughput, robust and reliable method for simultaneous analysis of five carotenoids, four chlorophylls and one tocopherol was developed for rapid screening large sample populations to facilitate molecular biology and plant breeding. Separation was achieved for 10 known analytes and
Andrew A Pascal et al.
Nature, 436(7047), 134-137 (2005-07-08)
In order to maximize their use of light energy in photosynthesis, plants have molecules that act as light-harvesting antennae, which collect light quanta and deliver them to the reaction centres, where energy conversion into a chemical form takes place. The
Eiichi Kotake-Nara et al.
Cancer letters, 220(1), 75-84 (2005-03-02)
Neoxanthin and fucoxanthin, which have the characteristic structure of 5,6-monoepoxide and an allenic bond, were previously found to reduce the viability of human prostate cancer cells most intensively among 15 dietary carotenoids tested. In the present study, the induction of
Alexander V Ruban et al.
Nature, 450(7169), 575-578 (2007-11-23)
Under conditions of excess sunlight the efficient light-harvesting antenna found in the chloroplast membranes of plants is rapidly and reversibly switched into a photoprotected quenched state in which potentially harmful absorbed energy is dissipated as heat, a process measured as
Miho Takemura et al.
Planta, 241(3), 699-710 (2014-12-04)
MpBHY codes for a carotene β-ring 3(,3')-hydroxylase responsible for both zeaxanthin and lutein biosynthesis in liverwort. MpCYP97C functions as an ε-ring hydroxylase (zeinoxanthin 3'-hydroxylase) to produce lutein in liverwort. Xanthophylls are oxygenated or hydroxylated carotenes that are most abundant in

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