AFCDB: alpha-Carotene (FDB013716)

Record Information

Version

1.0

Creation date

2010-04-08 22:10:52 UTC

Update date

2020-09-17 15:32:59 UTC

Primary ID

FDB013716

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

alpha-Carotene

Description

alpha Carotene belongs to the group of compounds known as carotenoids. More specifically carotenoids are classified as tetraterpenoids, being built from four terpene units (8 isoprene units) each containing 10 carbon atoms. As a result, carotenoids typically have a total of 40 carbon atoms. 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. There are more than 1100 known carotenoids. Carotenoids can be further categorized into two classes, xanthophylls (which contain oxygen) and carotenes (which are purely hydrocarbons and contain no oxygen). Carotenoids are among the most common pigments in nature and are natural lipid soluble antioxidants. alpha-Carotene is one of the primary isomers of carotene, although beta-carotene is the most abundant. There are six known carotene isomers including α-, β-, γ-, δ-, ε-, and ζ-carotene. These carotene isomers contain unsubstituted beta-ionone rings, which means they can be readily converted to retinol and vitamin A. In other words, they have pro-vitamin A activity. alpha-Carotene has less vitamin A activity than beta-carotene. This is because of its structure, as alpha-carotene it is converted to just one molecule of biologically active retinol after central cleavage, while beta-carotene is converted to two molecules after cleavage. Plants, fungi, and photosynthetic bacteria synthesize carotenes, while animals must obtain them as a dietary nutrient. In plants carotenes contribute to photosynthesis by transmitting the light energy they absorb to chlorophyll. They also protect plant tissues by helping to absorb the energy from singlet oxygen, an excited form of the oxygen molecule O2 which is formed during photosynthesis. alpha-Carotene is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. alpha-Carotene is found in many common orange-, yellow-, and green-colored fruits and vegetables such as carrots, pumpkins, squash, apricots, sweet potatoes, and beans. The concentration of alpha-Carotene is especially high in orange carrots and high serum concentrations are associated with high carrot intake. Other plants and foods that have high levels of alpha-carotene include cloves, shallots, cumin, wolfberries, cantaloupes, papaya, spinach, broccoli, turnip, avocado, green peas, orange and red peppers, and tomatoes. alpha-Carotene (along with beta-carotene) exhibits numerous beneficial health or pharmacological properties including antioxidant, anti-obesity, anti-cancer, anti-aging, anti-atherosclerotic and anti-sunburn properties as well as hepatoprotective, neuroprotective and improved vision and night blindness prevention (PMID: 27047317).

CAS Number

7488-99-5

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Synonym	Source
Not Available	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.00031 g/L	ALOGPS
logP	9.79	ALOGPS
logP	11.17	ChemAxon
logS	-6.2	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	191.88 m³·mol⁻¹	ChemAxon
Polarizability	71.41 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

(6R)-1,5,5-trimethyl-6-[(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/h11-14,17-23,25-28,37H,15-16,24,29-30H2,1-10H3/b12-11+,19-13+,20-14+,27-25+,28-26+,31-17+,32-18+,33-21+,34-22+/t37-/m0/s1

InChI Key

ANVAOWXLWRTKGA-NTXLUARGSA-N

Isomeric SMILES

C/C(=C\C=C\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C)/C=C/C=C(\C)/C=C/[C@H]1C(C)=CCCC1(C)C

Average Molecular Weight

536.8726

Monoisotopic Molecular Weight

536.438201792

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

alpha-carotene (CHEBI:35147 )
C40 isoprenoids (tetraterpenes) (LMPR01070011 )

Ontology

Foods

Fruits and vegetables:

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 187°	DFC
Boiling Point	Not Available
Experimental Water Solubility	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	[a]18643 +385 (C6H6)	DFC
Spectroscopic UV Data	471 () (hexane)	DFC
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Not Available

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0334190000-e05f79db2e425bfe8186	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000b-0769200000-81f1f88961c73bc3943a	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-004j-2689700000-a8528456aa6fa28bfb10	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0000090000-df0db1851156c1e36da6	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-0000090000-ac5ac3829642d0394d24	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-014i-0947360000-b2ba5d2cce5367c8424b	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0101090000-e6a413ebb46fe9a97e60	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000j-0336290000-c736f8dfebfeee67f7c1	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-0319000000-1e7037ebf4dd84aadb00	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-01pa-0269820000-f183b75adeec60119332	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-007t-0429400000-232c7e964986bedd5ad6	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-01q0-0229100000-971b11f97635708e0130	2021-09-24	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

3571861

ChEMBL ID

Not Available

KEGG Compound ID

C05433

Pubchem Compound ID

4369188

Pubchem Substance ID

Not Available

ChEBI ID

35147

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB03993

CRC / DFC (Dictionary of Food Compounds) ID

HVF46-E:JGG21-T

EAFUS ID

Not Available

Dr. Duke ID

ALPHA-CAROTENE|BETA-EPSILON-CAROTENE

BIGG ID

Not Available

KNApSAcK ID

C00003765

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

Alpha-Carotene

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

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
anti cancer	35610	A substance that inhibits or prevents the proliferation of neoplasms.	DUKE
anti proliferant			DUKE
colorant	37958		DUKE
provitamin A	50188	A substance that can be converted into a vitamin by animal tissues.	DUKE

Enzymes

Not Available

Pathways

Not Available

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

— 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.

alpha-Carotene (FDB013716)

Structure for FDB013716 (alpha-Carotene)