AFCDB: beta-Carotene (FDB014613)

Record Information

Version

1.0

Creation date

2010-04-08 22:11:22 UTC

Update date

2019-11-26 03:10:27 UTC

Primary ID

FDB014613

Secondary Accession Numbers

FDB030672

Chemical Information

FooDB Name

beta-Carotene

Description

beta-Carotene, also known as b-karotin or β-carotene, belongs to the class of organic compounds known as carotenes. These are a type of unsaturated hydrocarbons containing eight consecutive isoprene units. They 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. Thus, beta-carotene is considered to be an isoprenoid. Based on a literature review a significant number of articles have been published on beta-Carotene.

CAS Number

7235-40-7

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
Not Available	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.00039 g/L	ALOGPS
logP	9.72	ALOGPS
logP	11.12	ChemAxon
logS	-6.1	ALOGPS
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	0	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	0 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	191.61 m³·mol⁻¹	ChemAxon
Polarizability	72.05 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

C40H56

IUPAC name

1,3,3-trimethyl-2-[(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-1-ene

InChI Identifier

InChI=1S/C40H56/c1-31(19-13-21-33(3)25-27-37-35(5)23-15-29-39(37,7)8)17-11-12-18-32(2)20-14-22-34(4)26-28-38-36(6)24-16-30-40(38,9)10/h11-14,17-22,25-28H,15-16,23-24,29-30H2,1-10H3/b12-11+,19-13+,20-14+,27-25+,28-26+,31-17+,32-18+,33-21+,34-22+

InChI Key

OENHQHLEOONYIE-JLTXGRSLSA-N

Isomeric SMILES

C\C(\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C)=C/C=C/C=C(\C)/C=C/C=C(\C)/C=C/C1=C(C)CCCC1(C)C

Average Molecular Weight

536.888

Monoisotopic Molecular Weight

536.438201803

Classification

Description

Belongs to the class of organic compounds known as carotenes. These are a type of unsaturated hydrocarbons containing eight consecutive isoprene units. They 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.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Tetraterpenoids

Direct Parent

Carotenes

Alternative Parents

Substituents

Carotene
Branched unsaturated hydrocarbon
Cycloalkene
Cyclic olefin
Unsaturated aliphatic hydrocarbon
Unsaturated hydrocarbon
Olefin
Hydrocarbon
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

cyclic carotene (CHEBI:17579 )
C40 isoprenoids (tetraterpenes) (C02094 )
Carotenoids (C02094 )
C40 isoprenoids (tetraterpenes) (LMPR01070000 )

Ontology

No ontology term

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Solid
Physical Description	Not Available
Mass Composition	C 89.49%; H 10.51%	DFC
Melting Point	Mp 183° (sealed tube)	DFC
Boiling Point	Not Available
Experimental Water Solubility	0.0006 mg/mL	GREEN,FJ (1991)
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	520 () (CS2)	DFC
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
EI-MS	Mass Spectrum (Electron Ionization)	splash10-05mx-9810010000-9a261fb8602890c2481e	2015-03-01	View Spectrum
Predicted GC-MS	Carotene, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00di-3211290000-f968c686d39ae0f0fc50	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-0016-2794670000-c5bc2a4dbcd0f12cbf7f	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-0002-2687970000-782d048d873c21fc6b82	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-05ai-1009510000-585581456b10671692bd	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - FAB-EBEB (JMS-HX/HX 110A, JEOL) , Positive	splash10-05mx-2920010000-471219f3e66bafb29bee	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - , positive	splash10-0006-0144900000-2fa7b609c7300ff8aba3	2017-09-14	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0434190000-0f2f0f2c4af76e6c3322	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000b-0679100000-6f4450c8ade1963f9201	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000j-1789100000-6f2a7024e42303e7737a	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0000090000-cdea7c2d939f0c68b905	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-0000090000-530c81799c9daabdc9bf	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-014i-0968170000-ec71ee19e546088e3b05	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000j-0277960000-5b1eef16ffbc2ccd4b1e	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0081-0449400000-e362d306c4b151321fb6	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0iki-0149200000-5b858e5700ff1d750a4e	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0001090000-b0a4df7c3417e82842d7	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000j-0135090000-fb91b96b3605a056f12f	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0apj-0229000000-23e454829ef21fbedf66	2021-09-24	View Spectrum

NMR

Type	Description	View
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl₃, experimental)	Spectrum

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

17579

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB00561

CRC / DFC (Dictionary of Food Compounds) ID

JSX51-P:JSX51-P

EAFUS ID

531

Dr. Duke ID

BETA-BETA-CAROTENE|BETA-CAROTENE

BIGG ID

2264935

KNApSAcK ID

C00000919

HET ID

BCR

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

beta-Carotene

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Pubchem compound: 5356616

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Descriptor	ID	Definition	Reference
allergenic	50904	A chemical compound which causes the onset of an allergic reaction by interacting with any of the molecular pathways involved in an allergy.	DUKE
androgenic			DUKE
anti acne	50177	A drug used to treat or prevent skin disorders or for the routine care of skin.	DUKE
anti aging	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti arthritic	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti asthmatic	49167	A drug used to treat asthma.	DUKE
anti cancer	35610	A substance that inhibits or prevents the proliferation of neoplasms.	DUKE
anti carcinomic	35610	A substance that inhibits or prevents the proliferation of neoplasms.	DUKE
anti cervicaldysplasic	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti coronary	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti hyperkeratotic			DUKE
anti ichythyotic			DUKE
anti leukoplakic			DUKE
anti lipoperoxidant			DUKE
anti lupus	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti maculitic			DUKE
anti mastitic			DUKE
anti mutagenic			DUKE
antioxidant	22586	A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. In European countries, E-numbers for permitted antioxidant food additives are from E 300 to E 324.	DUKE
anti ozenic			DUKE
anti papillomic	22587	A substance that destroys or inhibits replication of viruses.	DUKE
anti photophobic	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti pityriasic			DUKE
anti premenstrual syndrome	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti porphyric			DUKE
anti proliferant			DUKE
anti psoriac	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti radicular			DUKE
anti rheumatic	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti stress	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
antitumor	35610	A substance that inhibits or prevents the proliferation of neoplasms.	DUKE
anti ulcer	49201	One of various classes of drugs with different action mechanisms used to treat or ameliorate peptic ulcer or irritation of the gastrointestinal tract.	DUKE
anti xerophthalmic	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
cancer preventive	35610	A substance that inhibits or prevents the proliferation of neoplasms.	DUKE
chemopreventive	35610	A substance that inhibits or prevents the proliferation of neoplasms.	DUKE
colorant	37958		DUKE
cyclooxygenase-1 inhibitor	50630	A cyclooxygenase inhibitor that interferes with the action of cyclooxygenase 1.	DUKE
cyclooxygenase-2 inhibitor	50629	A cyclooxygenase inhibitor that interferes with the action of cyclooxygenase 2.	DUKE
gastroprotective	55324	A drug used for its effects on the gastrointestinal system, e.g. controlling gastric acidity, regulating gastrointestinal motility and water flow, and improving digestion.	DUKE
immunostimulant	50847	A substance that augments, stimulates, activates, potentiates, or modulates the immune response at either the cellular or humoral level. A classical agent (Freund's adjuvant, BCG, Corynebacterium parvum, et al.) contains bacterial antigens. It could also be endogenous (e.g., histamine, interferon, transfer factor, tuftsin, interleukin-1). Its mode of action is either non-specific, resulting in increased immune responsiveness to a wide variety of antigens, or antigen-specific, i.e., affecting a restricted type of immune response to a narrow group of antigens. The therapeutic efficacy is related to its antigen-specific immunoadjuvanticity.	DUKE
interferon-synergist			DUKE
mucogenic			DUKE
phagocytotic			DUKE
prooxidant			DUKE
thymoprotective			DUKE
ubiquiot			DUKE

Enzymes

Not Available

Pathways

Name	SMPDB Link	KEGG Link
Retinol Metabolism	SMP00074	map00830

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Not Available

Files

MSDS

show

References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference

— Saxholt, E., et al. 'Danish food composition databank, revision 7.' Department of Nutrition, National Food Institute, Technical University of Denmark (2008).
— U.S. Department of Agriculture, Agricultural Research Service. 2008. USDA National Nutrient Database for Standard Reference, Release 21. Nutrient Data Laboratory Home Page.
— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.

beta-Carotene (FDB014613)

Structure for FDB014613 (beta-Carotene)