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Capsanthin

Capsanthin

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Also known as: 465-42-9, Paprika extract, All-trans-capsanthin, Capsanthin/capsorubin, (3r,3's,5'r)-3,3'-dihydroxy-beta,kappa-caroten-6'-one, Chebi:3375

Molecular Formula

C₄₀H₅₆O₃

Molecular Weight

584.9 g/mol

InChI Key

VYIRVAXUEZSDNC-RDJLEWNRSA-N

FDA UNII

420NY1J57N

capsanthin is a natural product found in Capsicum annuum, Lilium lancifolium, and Gallus gallus with data available.

1 2D Structure

Capsanthin

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(2E,4E,6E,8E,10E,12E,14E,16E,18E)-19-[(4R)-4-hydroxy-2,6,6-trimethylcyclohexen-1-yl]-1-[(1R,4S)-4-hydroxy-1,2,2-trimethylcyclopentyl]-4,8,13,17-tetramethylnonadeca-2,4,6,8,10,12,14,16,18-nonaen-1-one

2.1.2 InChI

InChI=1S/C40H56O3/c1-29(17-13-19-31(3)21-23-36-33(5)25-34(41)26-38(36,6)7)15-11-12-16-30(2)18-14-20-32(4)22-24-37(43)40(10)28-35(42)27-39(40,8)9/h11-24,34-35,41-42H,25-28H2,1-10H3/b12-11+,17-13+,18-14+,23-21+,24-22+,29-15+,30-16+,31-19+,32-20+/t34-,35+,40+/m1/s1

2.1.3 InChI Key

VYIRVAXUEZSDNC-RDJLEWNRSA-N

2.1.4 Canonical SMILES

CC1=C(C(CC(C1)O)(C)C)C=CC(=CC=CC(=CC=CC=C(C)C=CC=C(C)C=CC(=O)C2(CC(CC2(C)C)O)C)C)C

2.1.5 Isomeric SMILES

CC1=C(C(C[C@@H](C1)O)(C)C)/C=C/C(=C/C=C/C(=C/C=C/C=C(\C)/C=C/C=C(\C)/C=C/C(=O)[C@@]2(C[C@H](CC2(C)C)O)C)/C)/C

2.2 Other Identifiers

2.2.1 UNII

420NY1J57N

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Capsanthin, (3r,3's,5'r,13-cis)-isomer

2.3.2 Depositor-Supplied Synonyms

1. 465-42-9

2. Paprika Extract

3. All-trans-capsanthin

4. Capsanthin/capsorubin

5. (3r,3's,5'r)-3,3'-dihydroxy-beta,kappa-caroten-6'-one

6. Chebi:3375

7. 420ny1j57n

8. (2e,4e,6e,8e,10e,12e,14e,16e,18e)-19-[(4r)-4-hydroxy-2,6,6-trimethylcyclohexen-1-yl]-1-[(1r,4s)-4-hydroxy-1,2,2-trimethylcyclopentyl]-4,8,13,17-tetramethylnonadeca-2,4,6,8,10,12,14,16,18-nonaen-1-one

9. (2e,4e,6e,8e,10e,12e,14e,16e,18e)-1-((1r,4s)-4-hydroxy-1,2,2-trimethylcyclopentyl)-19-((r)-4-hydroxy-2,6,6-trimethylcyclohex-1-en-1-yl)-4,8,13,17-tetramethylnonadeca-2,4,6,8,10,12,14,16,18-nonaen-1-one

10. 3,3'-dihydroxy-beta,kappa-caroten-6'one

11. All Trans Capsanthin

12. Einecs 207-364-1

13. Unii-420ny1j57n

14. Hsdb 7977

15. Capsanthin [mi]

16. Beta,kappa-caroten-6'one, 3,3'dihydroxy-

17. Upcmld-dp025

18. Schembl117691

19. Spectrum1505276

20. Chembl1519371

21. Upcmld-dp025:001

22. Dtxsid10905012

23. Capsanthin, >=90.0% (hplc)

24. Zinc8221201

25. Capsanthin/capsorubin [inci]

26. Lmpr01070265

27. Mfcd31726206

28. Ccg-214238

29. Sdccgmls-0066894.p001

30. Ncgc00161603-01

31. Hy-125711

32. Cs-0093389

33. C08584

34. A827066

35. Q425431

36. Sr-05000002758

37. Sr-05000002758-1

38. 3,3'-dihydroxy-.beta.,.kappa.-caroten-6'on

39. Capsanthin (=paprika Extract)(vegetable Oil Solution)

40. .beta.,.kappa.-caroten-6'one, 3,3'dihydroxy-

41. (3r,3's,5'r)-3,3'-dihydroxy-.beta.,.kappa.-caroten-6'-one

42. (2e,4e,6e,8e,10e,12e,14e,16e,18e)-19-(4-hydroxy-2,6,6-trimethylcyclohexen-1-yl)-1-(4-hydroxy-1,2,2-trimethylcyclopentyl)-4,8,13,17-tetramethylnonadeca-2,4,6,8,10,12,14,16,18-nonaen-1-one

43. (2e,4e,6e,8e,10e,12e,14e,16e,18e)-19-[(4r)-4-hydroxy-2,6,6-trimethyl-1-cyclohexenyl]-1-[(1r,4s)-4-hydroxy-1,2,2-trimethylcyclopentyl]-4,8,13,17-tetramethyl-1-nonadeca-2,4,6,8,10,12,14,16,18-nonaenone

44. (2e,4e,6e,8e,10e,12e,14e,16e,18e)-4,8,13,17-tetramethyl-19-[(4r)-2,6,6-trimethyl-4-oxidanyl-cyclohexen-1-yl]-1-[(1r,4s)-1,2,2-trimethyl-4-oxidanyl-cyclopentyl]nonadeca-2,4,6,8,10,12,14,16,18-nonaen-1-one

45. 2,4,6,8,10,12,14,16,18-nonadecanonaen-1-one, 19-(4-hydroxy-2,6,6-trimethyl-1-cyclohexen-1-yl)-1-(4-hydroxy-1,2,2-trimethylcyclopentyl)-4,8,13,17-tetramethyl-, (all-e)-

46. 2,4,6,8,10,12,14,16,18-nonadecanonaen-1-one, 19-(4-hydroxy-2,6,6-trimethyl-1-cyclohexen-1-yl)-1-(5-hydroxy-1,2,2-trimethylcyclopentyl)-4,8,13,17-tetramethyl-

2.4 Create Date

2005-06-24

3 Chemical and Physical Properties

Molecular Formula	C₄₀H₅₆O₃
Molecular Weight	584.9 g/mol
XLogP3	10.6
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	3
Rotatable Bond Count	11
Exact Mass	584.42294564 g/mol
Monoisotopic Mass	584.42294564 g/mol
Topological Polar Surface Area	57.5 Å²
Heavy Atom Count	43
Formal Charge	0
Complexity	1310
Isotope Atom Count	0
Defined Atom Stereocenter Count	3
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	9
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Pharmacology and Biochemistry

4.1 Absorption, Distribution and Excretion

The pharmacokinetics of dietary capsanthin were determined in four male volunteers with plasma essentially free of capsanthin at the beginning of the study. They received paprika juice for 1 week, equivalent to three doses of 5.4 umol capsanthin/day, for a total of 16.2 umol/day. The level of capsanthin in plasma reached a plateau (0.10-0.12 umol/L) between day 2 and day 7, and capsanthin was not detectable in plasma by day 16. Capsanthin was distributed in the plasma lipoproteins after 1 week as follows: very low density lipoprotein, 13 +/- 3%; low-density lipoprotein, 44 +/- 3%; and high-density lipoprotein, 43 +/- 3%.

WHO/FAO; Joint Expert Committee on Food Additives (JECFA): Food Additive Series 60: Safety evaluation of certain food additives. Available from, As of June 22, 2011: https://www.inchem.org/pages/jecfa.html

In a /study/ involving the single ingestion of paprika juice (equivalent to 34.2 umol capsanthin) by the same men, the plasma concentration of capsanthin ranged from 0.10 to 0.29 umol/L at 8 hr after ingestion. In contrast, the elevation of the plasma concentration of an acyclic hydrocarbon carotenoid, lycopene, by a single ingestion of tomato soup (equivalent to 186.3 mmol lycopene) in the same subjects was minimal (0.02-0.06 mmol/L). The areas under the plasma concentration-time curves for capsanthin between 0 and 74 hr and for lycopene between 0 and 72 hr were 4.68 +/- 1.22 and 0.81 +/- 0.17 (umol.hr)/L, respectively. The half-lives were calculated to be 20.1 +/- 1.3 hr for capsanthin and 222 +/- 15 hr for lycopene. It was concluded that the clearance of capsanthin is much faster than that of lycopene, although capsanthin is transported into plasma lipoproteins in larger amounts.

The bioavailability of carotenoids from a paprika oleoresin (zeaxanthin, beta- cryptoxanthin, beta-carotene, capsanthin, capsorubin) was assessed in humans. After overnight fasting, nine volunteers ingested a single dose of a paprika oleoresin containing 6.4 mg zeaxanthin, 4.2 mg beta-cryptoxanthin, 6.2 mg beta-carotene, 35.0 mg capsanthin and 2.0 mg capsorubin. At different time points, the carotenoid pattern in the chylomicron fraction of whole blood was analyzed to evaluate carotenoid absorption. From the major carotenoids present in the paprika oleoresin, only zeaxanthin, beta-cryptoxanthin and beta-carotene were detectable in measurable amounts. Although the xanthophylls in paprika oleoresin were mainly present as mono- or diesters, only free zeaxanthin and beta-cryptoxanthin were found. The bioavailability of the pepper-specific carotenoids capsanthin and capsorubin from paprika oleoresin was found to be very low.

4.2 Metabolism/Metabolites

/A/ study in which rats were gavaged with a mixture of capsaicinoids /was reported/. These substances were extensively metabolized by a variety of metabolic pathways, including 1) hydrolysis of the acid-amide bond and deamination to form vanillylamine, 2) hydroxylation of the vanillyl ring, 3) oxidation of the hydroxyl group in the ring and 4) oxidation of the terminal carbon in the sidechain. /Capsaicinoids/

Later steps of carotenoid biosynthesis catalyzed by cyclase enzymes involve the formation of alpha, beta, and kappa-rings. Examination of the primary structure of lycopene beta-cyclase revealed 55% identity with that of antheraxanthin kappa-cyclase. Recombinant lycopene beta-cyclase afforded only beta-carotene, while recombinant antheraxanthin kappa-cyclase catalyzed the formation of beta-carotene from lycopene as well as the conversion of antheraxanthin into the kappa-carotenoid capsanthin. Since the formation of beta- and kappa-rings involves a transient carotenoid carbocation, this suggests that both cyclases initiate and/or neutralize the incipient carbocation by similar mechanisms. Several amine derivatives protonated at physiological pH were used to examine the molecular basis of this phenomenon. The beta-and kappa-cyclases displayed similar inhibition patterns. Affinity or photoaffinity labeling using p-dimethylamino-benzenediazonium fluoroborate, N,N-dimethyl-2-phenylaziridinium, and nicotine irreversibly inactivated both cyclase enzymes. Photoaffinity labeling using [H(3)]nicotine followed by radiosequence analysis and site-directed mutagenesis revealed the existence of two cyclase domains characterized by the presence of reactive aromatic and carboxylic amino acid residues. /Investigators/ propose that these residues represent the "negative point charges" involved in the coordination of the incipient carotenoid carbocations.

PMID:9328284 Bouvier F et al; 346 (1): 53-64 (1997)

4.3 Biological Half-Life

... In a /study/ involving the single ingestion of paprika juice (equivalent to 34.2 umol capsanthin) The half-lives /after a single ingestion of paprika juice (equivalent to 34.2 umol capsanthin)/ were calculated to be 20.1 +/- 1.3 hr for capsanthin and 222 +/- 15 hr for lycopene. ...