Showing Compound Cryptoxanthin-beta (FDB097255)

Record Information

Version

1.0

Creation date

2020-04-02 17:37:43 UTC

Update date

2020-09-17 15:30:39 UTC

Primary ID

FDB097255

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Cryptoxanthin-beta

Description

Alpha-cubebene, also known as cubebene, belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes that contain 15 carbon atoms and are comprised of three isoprene units. The biosynthesis of sesquiterpenes is known to occur mainly through the mevalonic acid pathway (MVA; PMID:17467679), in the cytoplasm. However, recent studies have found evidence of pathway crosstalk with the methyl-eritritol-phosphate (MEP) pathway in the cytosol (PMID: 23746261). Farnesyl diphosphate (FPP) is a key intermediate in the biosynthesis of cyclic sesquiterpenes. FPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. Alpha-Cubebene is one of the two Cubebene isomers, alpha- and beta-cubebene, both with the molecular formula C15H24, but differ only in the position of a double bond which is endocyclic (part of the five-membered ring) in Œ±-cubebene and exocyclic in Œ≤-cubebene. It was first isolated from Piper cubeba berries, known as cubebs, from which the name was derived. The volatile oil distilled from cubebs is a pale green or blue-yellow viscous liquid with a warm woody, slightly camphoraceous odor (consisting of both Œ±- and Œ≤-cubebene). In addition to cubeb berries, alpha-cubebene is also found in clove buds, fruit and seeds, cypress, lemon, lime, rosemary and tea tree oils and mandarins and oranges ( http://www.thegoodscentscompany.com/data/rw1054531.html#tooccur).

CAS Number

Not Available

Structure

MOL SDF PDB SMILES InChI

Synonyms

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Search:

Synonym	Source
(3R)-beta,beta-Caroten-3-ol	HMDB
(3R)-beta-Cryptoxanthin	HMDB
(3R)-Cryptoxanthin	HMDB
(3R)-Β,β-caroten-3-ol	HMDB
(3R)-Β-cryptoxanthin	HMDB
(R)-all-trans-beta-Caroten-3-ol	HMDB
(R)-all-trans-Β-caroten-3-ol	HMDB
3-Hydroxy-beta-carotene	HMDB
3-Hydroxy-β-carotene	HMDB
all-trans-beta-Cryptoxanthin	HMDB

Showing 1 to 10 of 33 entries

Predicted Properties

Property	Value	Source
Water Solubility	0.0005 g/L	ALOGPS
logP	9.08	ALOGPS
logP	9.74	ChemAxon
logS	-6	ALOGPS
pKa (Strongest Acidic)	18.91	ChemAxon
pKa (Strongest Basic)	-1.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	20.23 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	193.28 m³·mol⁻¹	ChemAxon
Polarizability	72.71 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C15H24

IUPAC name

(1R)-3,5,5-trimethyl-4-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-3,7,12,16-tetramethyl-18-(2,6,6-trimethylcyclohex-1-en-1-yl)octadeca-1,3,5,7,9,11,13,15,17-nonaen-1-yl]cyclohex-3-en-1-ol

InChI Identifier

InChI=1S/C15H24/c1-9(2)12-6-5-11(4)15-8-7-10(3)13(15)14(12)15/h7,9,11-14H,5-6,8H2,1-4H3/t11-,12+,13-,14-,15+/m1/s1

InChI Key

XUEHVOLRMXNRKQ-KHMAMNHCSA-N

Isomeric SMILES

CC(C)[C@@H]1CC[C@@H](C)[C@@]23CC=C(C)[C@@H]2[C@@H]13

Average Molecular Weight

204.357

Monoisotopic Molecular Weight

204.187800773

Classification

Description

Belongs to the class of organic compounds known as xanthophylls. These are carotenoids containing an oxygenated carotene backbone. Carotenes are characterized by the presence of two end-groups (mostly cyclohexene rings, but also cyclopentene rings or acyclic groups) linked by a long branched alkyl chain. Carotenes belonging form a subgroup of the carotenoids family. Xanthophylls arise by oxygenation of the carotene backbone.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Tetraterpenoids

Direct Parent

Xanthophylls

Alternative Parents

Substituents

Xanthophyll
Secondary alcohol
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Alcohol
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

carotenol (CHEBI:10362 )
C40 isoprenoids (tetraterpenes) (C08591 )
Carotenoids (C08591 )
C40 isoprenoids (tetraterpenes) (LMPR01070269 )

Ontology

No ontology term

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

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Property	Value	Reference
Boiling Point	Not Available
Charge	Not Available
Density	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Experimental Water Solubility	Not Available
Isoelectric point	Not Available
Mass Composition	Not Available
Melting Point	Not Available
Optical Rotation	Not Available

Showing 1 to 10 of 14 entries

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	, "beta-Cryptoxanthin,1TMS,#1" TMS, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - QIT 20V, positive	splash10-03e2-0000940000-3f294d1b8006a14a01ff	2020-07-21	View Spectrum
MS/MS	LC-MS/MS Spectrum - QIT 1V, positive	splash10-0gw0-0000590000-7d729e39216a9256dd6e	2020-07-21	View Spectrum
MS/MS	LC-MS/MS Spectrum - QTOF 4V, negative	splash10-001i-0100390000-6e3ca267c63ed4a7b967	2020-07-21	View Spectrum
MS/MS	LC-MS/MS Spectrum - QTOF 7V, positive	splash10-0udi-0410290000-a5c664cfd06c2fdd3324	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - QTOF 10V, positive	splash10-0udi-0510490000-039320bed3c92cf5f088	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - QTOF 15V, positive	splash10-0ik9-1940330000-b3ae219429ec53cbcd4d	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - QTOF 17V, positive	splash10-0ik9-1920320000-485587903906f2b18dcb	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - QTOF 20V, positive	splash10-0901-1930100000-4fd08614a2f7381f53d5	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - QTOF 23V, positive	splash10-0cka-1930000000-7f32a39aee17b0a4d9b7	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - QTOF 25V, positive	splash10-07i2-1920000000-83c4e90e75123b21d4e9	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - QTOF 27V, positive	splash10-0aos-1920000000-689e947f9f91e455db44	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - QTOF 33V, positive	splash10-0avj-2910000000-1f4da5545dbcc6e23443	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - QTOF 35V, positive	splash10-0apj-2910000000-2880fa73a258081c1514	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - QqQ 10V, positive	splash10-0udi-0000090000-0a3807d0b0e0fcf40e23	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - QqQ 12V, positive	splash10-0udi-0000190000-c531fb31efc607bca539	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - QqQ 14V, positive	splash10-0udi-0000290000-9dcfda517e5c18de5c13	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - QqQ 16V, positive	splash10-0w29-0100590000-8b0595fe54a9ba02ae84	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - QqQ 18V, positive	splash10-0w29-0531890000-cf871a68617fa4921636	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - QqQ 20V, positive	splash10-0ik9-0961640000-22863b9e3dbec1d44800	2020-07-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0f79-0423290000-bf7a8e40a11eff7bfe3c	2017-06-28	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0002-0649100000-9c3f50cab7f2d02e22fd	2017-06-28	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-002k-0569000000-8a2e2a50f957c26b3ab1	2017-06-28	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0000090000-d34ae69e503c3f381911	2017-06-28	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-0000090000-2fe3377fd40bc851dfc4	2017-06-28	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-000i-0546190000-d1d53215d44121d13684	2017-06-28	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

Not Available

ChEMBL ID

Not Available

KEGG Compound ID

Not Available

Pubchem Compound ID

Not Available

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

Not Available

CRC / DFC (Dictionary of Food Compounds) ID

Not Available

EAFUS ID

Not Available

Dr. Duke ID

Not Available

BIGG ID

Not Available

KNApSAcK ID

Not Available

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Not Available

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

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Food	Content Range	Average	Reference

Apricot	Expected but not quantified	Not Available	PHYTOHUB
Common sage	Expected but not quantified	Not Available	PHYTOHUB
Corn	Expected but not quantified	Not Available	PHYTOHUB
Dill	Expected but not quantified	Not Available	PHYTOHUB
Green bell pepper	Expected but not quantified	Not Available	PHYTOHUB
Guava	Expected but not quantified	Not Available	PHYTOHUB
Mandarin orange (Clementine, Tangerine)	Expected but not quantified	Not Available	PHYTOHUB
Mango	Expected but not quantified	Not Available	PHYTOHUB
Orange bell pepper	Expected but not quantified	Not Available	PHYTOHUB
Papaya	Expected but not quantified	Not Available	PHYTOHUB