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C6368

Sigma-Aldrich

β-Cryptoxanthin

≥97% (TLC)

Synonym(s):

Caricaxanthin, Hydroxy-β-carotene

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About This Item

Empirical Formula (Hill Notation):
C40H56O
CAS Number:
Molecular Weight:
552.87
UNSPSC Code:
12352205
PubChem Substance ID:
NACRES:
NA.79

Quality Level

Assay

≥97% (TLC)

form

powder

color

faint red to very dark red

mp

169-170 °C

solubility

chloroform: 1 mg/mL

storage temp.

−20°C

SMILES string

CC(=C\C=C\C=C(C)\C=C\C=C(C)\C=C\C1=C(C)C[C@@H](O)CC1(C)C)/C=C/C=C(C)/C=C/C2=C(C)CCCC2(C)C

InChI

1S/C40H56O/c1-30(18-13-20-32(3)23-25-37-34(5)22-15-27-39(37,7)8)16-11-12-17-31(2)19-14-21-33(4)24-26-38-35(6)28-36(41)29-40(38,9)10/h11-14,16-21,23-26,36,41H,15,22,27-29H2,1-10H3/b12-11+,18-13+,19-14+,25-23+,26-24+,30-16+,31-17+,32-20+,33-21+/t36-/m1/s1

InChI key

DMASLKHVQRHNES-FKKUPVFPSA-N

General description

β-Cryptoxanthin is an oxygen-containing carotenoid and is a member of the xanthophyll family. It is one of the major sources of vitamin A and is present in fruits such as oranges, tangerines and papayas. In addition, it is also found in corn, peas and some animal products such as egg yolk and butter.

Application

β-Cryptoxanthin has also been used to study its effect on the production of immunoglobulins in Peyer′s patch cells ex- vivo. It has also been used as a standard in high-performance liquid chromatography (HPLC analysis).(5)

Biochem/physiol Actions

β-Cryptoxanthin exhibits potential-anabolic effect on bone calcification by stimulating osteoblastic bone formation and inhibiting osteoclastic bone resorption in vitro. It acts as an antioxidant and avoids free radical damage to biomolecules such as lipids, proteins and nucleic acids. High dietary intake of β-cryptoxanthin reduces the risk of developing rheumatoid arthritis and lung cancer.
Carotenoid pigment with antioxidant functionality. In vivo conversion of β-cryptoxanthin to retinol can occur in humans. Inhibits carcinogenic induced urinary bladder cancer in experimental animal models.

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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J Libien et al.
Journal of the neurological sciences, 372, 78-84 (2016-12-27)
Vitamin A and its metabolites (called retinoids) have been thought to play a role in the development of idiopathic intracranial hypertension (IIH). The IIH Treatment Trial (IIHTT) showed the efficacy of acetazolamide (ACZ) in improving visual field function, papilledema grade
The chemopreventive effect of beta-cryptoxanthin from mandarin on human stomach cells (BGC-823)
Wu C, et al.
Food Chemistry, 136(3-4), 1122-1129 (2013)
Capsicum extract and its constituents modulated the production of immunoglobulins in Peyer?s patch cells ex vivo
Yamaguchi M, et al.
Journal of functional foods, 2(4), 255-262 (2010)
beta-Cryptoxanthin selectively increases in human chylomicrons upon ingestion of tangerine concentrate rich in beta-cryptoxanthin esters
Wingerath T
Archives of Biochemistry and Biophysics, 324(2), 385-390 (1995)
Role of carotenoid beta-cryptoxanthin in bone homeostasis
Yamaguchi M, et al.
Journal of Biomedical Science, 19(1), 36-36 (2012)

Articles

All-trans retinoic acid (RA, ATRA) is a pleiotropic activation factor that regulates genes associated with normal vertebrate cellular processes such as cell differentiation, cell proliferation, apoptosis, and embryonic development.

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